NPASS Compound

Structure

CID312215 OpenBabel06191716122D 35 37 0 0 1 0 0 0 0 0999 V2000 -1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5981 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 19 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 18 2 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 24 1 0 0 0 0 17 30 1 0 0 0 0 19 21 1 0 0 0 0 20 10 1 1 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 1 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 29 1 1 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	532.535
LogP:	5.485
LogD:	2.702
LogS:	-3.932
# Rotatable Bonds:	9
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	5.018
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.726
MDCK Permeability:	4.942257419315865e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.67
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	95.38111114501953%
Volume Distribution (VD):	0.512
Pgp-substrate:	4.462155818939209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.396
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	2.301
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.121
Skin Sensitization:	0.117
Carcinogencity:	0.235
Eye Corrosion:	0.013
Eye Irritation:	0.026
Respiratory Toxicity:	0.936

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC312215

Natural Product ID:	NPC312215
*Common Name:**	Poricoic Acid G
IUPAC Name:	(2R)-2-[(2R,3R,3aR,6S,7S,9bR)-6-(2-carboxyethyl)-2-hydroxy-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,7,8,9-octahydrocyclopenta[a]naphthalen-3-yl]-6-methylhept-5-enoic acid
Synonyms:	Poricoic Acid G
Standard InCHIKey:	VPTZOSBKEDUOFE-KXGBKNTBSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-18(2)9-8-10-20(27(34)35)26-24(31)17-30(7)23-12-11-21(19(3)4)28(5,15-14-25(32)33)22(23)13-16-29(26,30)6/h9,20-21,24,26,31H,3,8,10-17H2,1-2,4-7H3,(H,32,33)(H,34,35)/t20-,21+,24-,26+,28+,29-,30+/m1/s1
SMILES:	OC(=O)CC[C@@]1(C)[C@@H](CCC2=C1CC[C@]1([C@@]2(C)C[C@H]([C@@H]1[C@H](C(=O)O)CCC=C(C)C)O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL138450
PubChem CID:	5471966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	60
IC50	10
Others	5

Activity Type	# Activity
Cell Line	68
NON-MOLECULAR	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	39.3	nM	PMID[522317]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[522318]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	39.3	nM	PMID[522318]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	32600.0	nM	PMID[522319]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	32600.0	nM	PMID[522320]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[522320]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	>	100000.0	nM	PMID[522320]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	100000.0	nM	PMID[522320]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	100000.0	nM	PMID[522320]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	100000.0	nM	PMID[522320]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	86297.85	nM	PMID[522321]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	52360.04	nM	PMID[522321]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	75162.29	nM	PMID[522321]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	87297.14	nM	PMID[522321]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	32062.69	nM	PMID[522321]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	39.26	nM	PMID[522321]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	59292.53	nM	PMID[522321]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	92682.98	nM	PMID[522321]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	53210.83	nM	PMID[522321]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	53210.83	nM	PMID[522321]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	22438.82	nM	PMID[522321]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	45394.16	nM	PMID[522321]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	46025.66	nM	PMID[522321]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	29376.5	nM	PMID[522321]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	44157.04	nM	PMID[522321]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	47424.2	nM	PMID[522321]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	99770.01	nM	PMID[522321]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	88715.6	nM	PMID[522321]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	61235.04	nM	PMID[522321]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	71944.9	nM	PMID[522321]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	70307.23	nM	PMID[522321]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	42072.66	nM	PMID[522321]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	60534.09	nM	PMID[522321]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	38636.7	nM	PMID[522321]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	54075.43	nM	PMID[522321]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	94841.85	nM	PMID[522321]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	44565.62	nM	PMID[522321]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	45603.69	nM	PMID[522321]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	46773.51	nM	PMID[522321]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	83560.3	nM	PMID[522321]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	42559.84	nM	PMID[522321]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	50350.06	nM	PMID[522321]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	85901.35	nM	PMID[522321]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[522321]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	63241.19	nM	PMID[522321]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	57279.6	nM	PMID[522321]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	47424.2	nM	PMID[522321]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	66834.39	nM	PMID[522321]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	41399.97	nM	PMID[522321]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	52844.53	nM	PMID[522321]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	39.3	nM	PMID[522322]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[522318]
NPT2	Others	Unspecified		Activity	=	16.0	%	PMID[522318]
NPT2	Others	Unspecified		Activity	=	55.9	%	PMID[522318]
NPT2	Others	Unspecified		Activity	=	82.8	%	PMID[522318]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[522319]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[522320]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC312215 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1140
0.2-0.3	5872
0.3-0.4	15540
0.4-0.5	7068
0.5-0.6	6851
0.6-0.7	4971
0.7-0.8	972
0.8-0.85	81
0.85-0.9	23
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC294480
0.9877	High Similarity	NPC212843
0.9643	High Similarity	NPC46281
0.9639	High Similarity	NPC48866
0.9639	High Similarity	NPC247406
0.9639	High Similarity	NPC183546
0.9524	High Similarity	NPC54689
0.9524	High Similarity	NPC155479
0.9419	High Similarity	NPC66429
0.9419	High Similarity	NPC152897
0.9412	High Similarity	NPC123854
0.9302	High Similarity	NPC45269
0.9302	High Similarity	NPC154101
0.9302	High Similarity	NPC23434
0.9205	High Similarity	NPC45324
0.9205	High Similarity	NPC263347
0.9205	High Similarity	NPC162001
0.9205	High Similarity	NPC222845
0.9195	High Similarity	NPC470376
0.9195	High Similarity	NPC470375
0.9195	High Similarity	NPC243866
0.9101	High Similarity	NPC155676
0.9091	High Similarity	NPC7165
0.8989	High Similarity	NPC184848
0.8989	High Similarity	NPC69548
0.8989	High Similarity	NPC20546
0.8929	High Similarity	NPC165064
0.8901	High Similarity	NPC477813
0.8901	High Similarity	NPC186810
0.8901	High Similarity	NPC48647
0.8837	High Similarity	NPC187376
0.8837	High Similarity	NPC159046
0.8837	High Similarity	NPC233836
0.8837	High Similarity	NPC167877
0.8824	High Similarity	NPC474218
0.8791	High Similarity	NPC469432
0.8791	High Similarity	NPC57416
0.8791	High Similarity	NPC107243
0.8778	High Similarity	NPC469599
0.8764	High Similarity	NPC206810
0.8736	High Similarity	NPC242864
0.8721	High Similarity	NPC28252
0.8721	High Similarity	NPC55309
0.8721	High Similarity	NPC155011
0.8706	High Similarity	NPC82902
0.869	High Similarity	NPC133391
0.8681	High Similarity	NPC173272
0.8652	High Similarity	NPC150383
0.8652	High Similarity	NPC297265
0.8636	High Similarity	NPC214387
0.8636	High Similarity	NPC102414
0.8636	High Similarity	NPC476733
0.8636	High Similarity	NPC477943
0.8636	High Similarity	NPC84271
0.8636	High Similarity	NPC475921
0.8636	High Similarity	NPC474704
0.8636	High Similarity	NPC215029
0.8636	High Similarity	NPC77168
0.8621	High Similarity	NPC142361
0.8621	High Similarity	NPC96496
0.8621	High Similarity	NPC317590
0.8621	High Similarity	NPC474684
0.8617	High Similarity	NPC195290
0.8617	High Similarity	NPC204450
0.8602	High Similarity	NPC218383
0.8587	High Similarity	NPC475894
0.8571	High Similarity	NPC38350
0.8571	High Similarity	NPC201912
0.8571	High Similarity	NPC48330
0.8556	High Similarity	NPC25750
0.8554	High Similarity	NPC196827
0.8554	High Similarity	NPC477371
0.8554	High Similarity	NPC274996
0.8539	High Similarity	NPC175628
0.8539	High Similarity	NPC477147
0.8539	High Similarity	NPC469400
0.8539	High Similarity	NPC148414
0.8539	High Similarity	NPC111585
0.8539	High Similarity	NPC477149
0.8539	High Similarity	NPC171441
0.8526	High Similarity	NPC236390
0.8511	High Similarity	NPC474327
0.8506	High Similarity	NPC469994
0.8495	Intermediate Similarity	NPC235464
0.8495	Intermediate Similarity	NPC197386
0.8495	Intermediate Similarity	NPC166745
0.8488	Intermediate Similarity	NPC473246
0.8488	Intermediate Similarity	NPC100391
0.8471	Intermediate Similarity	NPC296367
0.8471	Intermediate Similarity	NPC260956
0.8462	Intermediate Similarity	NPC469406
0.8444	Intermediate Similarity	NPC212301
0.8444	Intermediate Similarity	NPC26888
0.8444	Intermediate Similarity	NPC86266
0.8444	Intermediate Similarity	NPC110657
0.8444	Intermediate Similarity	NPC189520
0.8438	Intermediate Similarity	NPC477812
0.8427	Intermediate Similarity	NPC474889
0.8391	Intermediate Similarity	NPC474083
0.8372	Intermediate Similarity	NPC310470
0.8372	Intermediate Similarity	NPC83569
0.8372	Intermediate Similarity	NPC477373
0.8372	Intermediate Similarity	NPC245866
0.8372	Intermediate Similarity	NPC69279
0.837	Intermediate Similarity	NPC241156
0.8353	Intermediate Similarity	NPC477372
0.8353	Intermediate Similarity	NPC147066
0.8352	Intermediate Similarity	NPC472942
0.8352	Intermediate Similarity	NPC107674
0.8352	Intermediate Similarity	NPC170220
0.8352	Intermediate Similarity	NPC141497
0.8352	Intermediate Similarity	NPC470224
0.8333	Intermediate Similarity	NPC69622
0.8333	Intermediate Similarity	NPC471896
0.8333	Intermediate Similarity	NPC44240
0.8333	Intermediate Similarity	NPC320026
0.8333	Intermediate Similarity	NPC140723
0.8315	Intermediate Similarity	NPC328313
0.8315	Intermediate Similarity	NPC28227
0.8315	Intermediate Similarity	NPC470417
0.8298	Intermediate Similarity	NPC10364
0.8295	Intermediate Similarity	NPC94755
0.8295	Intermediate Similarity	NPC80590
0.828	Intermediate Similarity	NPC42042
0.828	Intermediate Similarity	NPC95565
0.828	Intermediate Similarity	NPC472941
0.828	Intermediate Similarity	NPC456
0.828	Intermediate Similarity	NPC125622
0.8276	Intermediate Similarity	NPC59453
0.8276	Intermediate Similarity	NPC214043
0.8276	Intermediate Similarity	NPC221758
0.8276	Intermediate Similarity	NPC476038
0.8276	Intermediate Similarity	NPC161423
0.8276	Intermediate Similarity	NPC329043
0.8276	Intermediate Similarity	NPC227064
0.8276	Intermediate Similarity	NPC58841
0.8276	Intermediate Similarity	NPC194937
0.8276	Intermediate Similarity	NPC321187
0.8276	Intermediate Similarity	NPC85774
0.8261	Intermediate Similarity	NPC49670
0.8261	Intermediate Similarity	NPC166906
0.8261	Intermediate Similarity	NPC111015
0.8256	Intermediate Similarity	NPC240302
0.8247	Intermediate Similarity	NPC472228
0.8247	Intermediate Similarity	NPC472227
0.8242	Intermediate Similarity	NPC107690
0.8229	Intermediate Similarity	NPC473928
0.8222	Intermediate Similarity	NPC474570
0.8222	Intermediate Similarity	NPC128496
0.8222	Intermediate Similarity	NPC474679
0.8222	Intermediate Similarity	NPC310236
0.8222	Intermediate Similarity	NPC2983
0.8222	Intermediate Similarity	NPC76879
0.8214	Intermediate Similarity	NPC321514
0.8211	Intermediate Similarity	NPC205899
0.8211	Intermediate Similarity	NPC51370
0.8211	Intermediate Similarity	NPC287833
0.8211	Intermediate Similarity	NPC476274
0.8202	Intermediate Similarity	NPC477926
0.8202	Intermediate Similarity	NPC90652
0.8202	Intermediate Similarity	NPC136548
0.8202	Intermediate Similarity	NPC134197
0.8191	Intermediate Similarity	NPC18319
0.8182	Intermediate Similarity	NPC283733
0.8182	Intermediate Similarity	NPC471224
0.8182	Intermediate Similarity	NPC329738
0.8172	Intermediate Similarity	NPC318282
0.8172	Intermediate Similarity	NPC469995
0.8172	Intermediate Similarity	NPC174948
0.8172	Intermediate Similarity	NPC317586
0.8172	Intermediate Similarity	NPC472932
0.8172	Intermediate Similarity	NPC173875
0.8172	Intermediate Similarity	NPC470016
0.8161	Intermediate Similarity	NPC278648
0.8161	Intermediate Similarity	NPC168188
0.8161	Intermediate Similarity	NPC477852
0.8161	Intermediate Similarity	NPC470015
0.8161	Intermediate Similarity	NPC474748
0.8161	Intermediate Similarity	NPC476082
0.8152	Intermediate Similarity	NPC109414
0.8152	Intermediate Similarity	NPC250575
0.8152	Intermediate Similarity	NPC470254
0.814	Intermediate Similarity	NPC473420
0.814	Intermediate Similarity	NPC327002
0.8132	Intermediate Similarity	NPC193750
0.8132	Intermediate Similarity	NPC18872
0.8132	Intermediate Similarity	NPC290614
0.8132	Intermediate Similarity	NPC289213
0.8132	Intermediate Similarity	NPC273621
0.8132	Intermediate Similarity	NPC227467
0.8132	Intermediate Similarity	NPC210037
0.8132	Intermediate Similarity	NPC477872
0.8132	Intermediate Similarity	NPC7260
0.8132	Intermediate Similarity	NPC120968
0.8125	Intermediate Similarity	NPC99411
0.8125	Intermediate Similarity	NPC224720
0.8125	Intermediate Similarity	NPC476240
0.8125	Intermediate Similarity	NPC476223
0.8118	Intermediate Similarity	NPC327674
0.8118	Intermediate Similarity	NPC158846

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC312215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1730
0.2-0.3	4039
0.3-0.4	2204
0.4-0.5	535
0.5-0.6	200
0.6-0.7	205
0.7-0.8	87
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD6399	Phase 3
0.8444	Intermediate Similarity	NPD5281	Approved
0.8444	Intermediate Similarity	NPD5284	Approved
0.8276	Intermediate Similarity	NPD3666	Approved
0.8276	Intermediate Similarity	NPD3133	Approved
0.8276	Intermediate Similarity	NPD3665	Phase 1
0.8276	Intermediate Similarity	NPD4786	Approved
0.8191	Intermediate Similarity	NPD6083	Phase 2
0.8191	Intermediate Similarity	NPD6084	Phase 2
0.8172	Intermediate Similarity	NPD5695	Phase 3
0.809	Intermediate Similarity	NPD7334	Approved
0.809	Intermediate Similarity	NPD6684	Approved
0.809	Intermediate Similarity	NPD7146	Approved
0.809	Intermediate Similarity	NPD7521	Approved
0.809	Intermediate Similarity	NPD5330	Approved
0.809	Intermediate Similarity	NPD6409	Approved
0.8046	Intermediate Similarity	NPD3667	Approved
0.8022	Intermediate Similarity	NPD4753	Phase 2
0.798	Intermediate Similarity	NPD7128	Approved
0.798	Intermediate Similarity	NPD6402	Approved
0.798	Intermediate Similarity	NPD5739	Approved
0.798	Intermediate Similarity	NPD6675	Approved
0.7957	Intermediate Similarity	NPD4202	Approved
0.7921	Intermediate Similarity	NPD6372	Approved
0.7921	Intermediate Similarity	NPD6373	Approved
0.7917	Intermediate Similarity	NPD5696	Approved
0.7912	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6903	Approved
0.7889	Intermediate Similarity	NPD3618	Phase 1
0.7889	Intermediate Similarity	NPD5279	Phase 3
0.7841	Intermediate Similarity	NPD4221	Approved
0.7841	Intermediate Similarity	NPD4223	Phase 3
0.7826	Intermediate Similarity	NPD5328	Approved
0.7822	Intermediate Similarity	NPD6899	Approved
0.7822	Intermediate Similarity	NPD6881	Approved
0.7822	Intermediate Similarity	NPD7320	Approved
0.7816	Intermediate Similarity	NPD5368	Approved
0.7812	Intermediate Similarity	NPD4755	Approved
0.7791	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5210	Approved
0.7789	Intermediate Similarity	NPD4629	Approved
0.7778	Intermediate Similarity	NPD5329	Approved
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD6649	Approved
0.7767	Intermediate Similarity	NPD6650	Approved
0.7753	Intermediate Similarity	NPD5362	Discontinued
0.7727	Intermediate Similarity	NPD5369	Approved
0.7723	Intermediate Similarity	NPD5697	Approved
0.7723	Intermediate Similarity	NPD5701	Approved
0.7717	Intermediate Similarity	NPD6672	Approved
0.7717	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD6098	Approved
0.7692	Intermediate Similarity	NPD4694	Approved
0.7692	Intermediate Similarity	NPD5690	Phase 2
0.7692	Intermediate Similarity	NPD5280	Approved
0.767	Intermediate Similarity	NPD6883	Approved
0.767	Intermediate Similarity	NPD7102	Approved
0.767	Intermediate Similarity	NPD7290	Approved
0.7667	Intermediate Similarity	NPD4197	Approved
0.766	Intermediate Similarity	NPD6050	Approved
0.766	Intermediate Similarity	NPD7515	Phase 2
0.766	Intermediate Similarity	NPD6079	Approved
0.766	Intermediate Similarity	NPD8034	Phase 2
0.766	Intermediate Similarity	NPD8035	Phase 2
0.7653	Intermediate Similarity	NPD5285	Approved
0.7653	Intermediate Similarity	NPD4700	Approved
0.7653	Intermediate Similarity	NPD5286	Approved
0.7653	Intermediate Similarity	NPD4696	Approved
0.7647	Intermediate Similarity	NPD6011	Approved
0.764	Intermediate Similarity	NPD4270	Approved
0.764	Intermediate Similarity	NPD4269	Approved
0.764	Intermediate Similarity	NPD6435	Approved
0.7634	Intermediate Similarity	NPD6673	Approved
0.7634	Intermediate Similarity	NPD6904	Approved
0.7634	Intermediate Similarity	NPD6080	Approved
0.7604	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8130	Phase 1
0.7596	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6847	Approved
0.7596	Intermediate Similarity	NPD6869	Approved
0.7596	Intermediate Similarity	NPD6617	Approved
0.7576	Intermediate Similarity	NPD5223	Approved
0.7573	Intermediate Similarity	NPD6012	Approved
0.7573	Intermediate Similarity	NPD6014	Approved
0.7573	Intermediate Similarity	NPD6013	Approved
0.7558	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4788	Approved
0.7553	Intermediate Similarity	NPD5207	Approved
0.7553	Intermediate Similarity	NPD5692	Phase 3
0.7528	Intermediate Similarity	NPD4692	Approved
0.7528	Intermediate Similarity	NPD4139	Approved
0.7526	Intermediate Similarity	NPD4697	Phase 3
0.7524	Intermediate Similarity	NPD6882	Approved
0.7524	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7474	Intermediate Similarity	NPD5694	Approved
0.7474	Intermediate Similarity	NPD6411	Approved
0.7473	Intermediate Similarity	NPD3668	Phase 3
0.7449	Intermediate Similarity	NPD7902	Approved
0.7442	Intermediate Similarity	NPD7339	Approved
0.7442	Intermediate Similarity	NPD6942	Approved
0.7426	Intermediate Similarity	NPD5174	Approved
0.7426	Intermediate Similarity	NPD5175	Approved
0.7426	Intermediate Similarity	NPD4754	Approved
0.7416	Intermediate Similarity	NPD7525	Registered
0.7416	Intermediate Similarity	NPD4820	Approved
0.7416	Intermediate Similarity	NPD4822	Approved
0.7416	Intermediate Similarity	NPD4821	Approved
0.7416	Intermediate Similarity	NPD4252	Approved
0.7416	Intermediate Similarity	NPD4819	Approved
0.7391	Intermediate Similarity	NPD5363	Approved
0.7391	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4268	Approved
0.7386	Intermediate Similarity	NPD4271	Approved
0.7379	Intermediate Similarity	NPD6412	Phase 2
0.7374	Intermediate Similarity	NPD7638	Approved
0.7368	Intermediate Similarity	NPD5785	Approved
0.7363	Intermediate Similarity	NPD5331	Approved
0.7363	Intermediate Similarity	NPD5332	Approved
0.7353	Intermediate Similarity	NPD5141	Approved
0.7347	Intermediate Similarity	NPD5221	Approved
0.7347	Intermediate Similarity	NPD5222	Approved
0.7347	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5208	Approved
0.7333	Intermediate Similarity	NPD4790	Discontinued
0.732	Intermediate Similarity	NPD7748	Approved
0.7312	Intermediate Similarity	NPD5786	Approved
0.7312	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7640	Approved
0.73	Intermediate Similarity	NPD7639	Approved
0.7294	Intermediate Similarity	NPD4243	Approved
0.7292	Intermediate Similarity	NPD5693	Phase 1
0.729	Intermediate Similarity	NPD4632	Approved
0.7282	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD4768	Approved
0.7282	Intermediate Similarity	NPD4767	Approved
0.7273	Intermediate Similarity	NPD5173	Approved
0.7273	Intermediate Similarity	NPD6116	Phase 1
0.7263	Intermediate Similarity	NPD6051	Approved
0.7263	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6101	Approved
0.7222	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6053	Discontinued
0.7188	Intermediate Similarity	NPD4096	Approved
0.7182	Intermediate Similarity	NPD6335	Approved
0.7159	Intermediate Similarity	NPD6117	Approved
0.7158	Intermediate Similarity	NPD4518	Approved
0.7156	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6001	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7126	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4784	Approved
0.7126	Intermediate Similarity	NPD6926	Approved
0.7126	Intermediate Similarity	NPD4785	Approved
0.7126	Intermediate Similarity	NPD6924	Approved
0.7117	Intermediate Similarity	NPD7100	Approved
0.7117	Intermediate Similarity	NPD7101	Approved
0.7111	Intermediate Similarity	NPD4195	Approved
0.7091	Intermediate Similarity	NPD6009	Approved
0.7091	Intermediate Similarity	NPD6317	Approved
0.7083	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5654	Approved
0.7041	Intermediate Similarity	NPD5133	Approved
0.7041	Intermediate Similarity	NPD5778	Approved
0.7041	Intermediate Similarity	NPD5779	Approved
0.7033	Intermediate Similarity	NPD4748	Discontinued
0.7027	Intermediate Similarity	NPD6314	Approved
0.7027	Intermediate Similarity	NPD6313	Approved
0.7009	Intermediate Similarity	NPD4634	Approved
0.7009	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5249	Phase 3
0.7009	Intermediate Similarity	NPD5247	Approved
0.7009	Intermediate Similarity	NPD5135	Approved
0.7009	Intermediate Similarity	NPD5251	Approved
0.7009	Intermediate Similarity	NPD5169	Approved
0.7009	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD6118	Approved
0.7	Intermediate Similarity	NPD6697	Approved
0.7	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD6115	Approved
0.6991	Remote Similarity	NPD6908	Approved
0.6991	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6909	Approved
0.6989	Remote Similarity	NPD7154	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data