NPASS Compound

Structure

CID165608 OpenBabel06191715532D 24 29 0 0 1 0 0 0 0 0999 V2000 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7812 0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 1 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 1 0 0 0 13 19 1 0 0 0 0 14 19 1 1 0 0 0 14 22 1 0 0 0 0 15 20 1 1 0 0 0 15 23 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 18 4 1 1 0 0 0 19 9 1 1 0 0 0 19 22 1 0 0 0 0 20 12 1 6 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	333.025
LogP:	4.647
LogD:	4.427
LogS:	-5.32
# Rotatable Bonds:	0
TPSA:	51.36
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	5.761
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.228
MDCK Permeability:	4.465831443667412e-05
Pgp-inhibitor:	0.126
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.831

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	90.55724334716797%
Volume Distribution (VD):	2.25
Pgp-substrate:	10.417017936706543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.315
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.45
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.355
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	9.022
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.313
Skin Sensitization:	0.576
Carcinogencity:	0.046
Eye Corrosion:	0.825
Eye Irritation:	0.749
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC165608

Natural Product ID:	NPC165608
*Common Name:**	Jolkinolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SOVOCMGDFRGRKF-MCDHERAVSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-10-12-14-19(22-14)9-6-11-17(2,3)7-5-8-18(11,4)13(19)15-20(12,23-15)24-16(10)21/h11,13-15H,5-9H2,1-4H3/t11-,13+,14-,15-,18-,19+,20-/m1/s1
SMILES:	CC1=C2[C@@H]3[C@@]4(CC[C@@H]5C(C)(C)CCC[C@@]5(C)[C@@H]4[C@@H]4[C@]2(O4)OC1=O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404387
PubChem CID:	161954
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO25280	Suregada glomerulata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18205316]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO25280	Suregada glomerulata	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23993676]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25280	Suregada glomerulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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	58
IC50	15
MIC	1
Others	3

Activity Type	# Activity
Cell Line	71
CELL-LINE	1
NON-MOLECULAR	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6.1	ug.mL-1	PMID[528596]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	6.88	ug.mL-1	PMID[528596]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	5.09	ug.mL-1	PMID[528596]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	2697.74	nM	PMID[528597]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	2648.5	nM	PMID[528597]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	3097.42	nM	PMID[528597]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	3155.0	nM	PMID[528597]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	1570.36	nM	PMID[528597]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	2811.9	nM	PMID[528597]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	28575.91	nM	PMID[528597]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	3944.57	nM	PMID[528597]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	5649.37	nM	PMID[528597]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	2494.59	nM	PMID[528597]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	3523.71	nM	PMID[528597]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	18407.72	nM	PMID[528597]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	7709.03	nM	PMID[528597]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	7852.36	nM	PMID[528597]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	12445.15	nM	PMID[528597]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2606.15	nM	PMID[528597]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	9616.12	nM	PMID[528597]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	3013.01	nM	PMID[528597]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	3013.01	nM	PMID[528597]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	3388.44	nM	PMID[528597]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	5164.16	nM	PMID[528597]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	3388.44	nM	PMID[528597]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	2779.71	nM	PMID[528597]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	3176.87	nM	PMID[528597]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1823.9	nM	PMID[528597]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	10641.43	nM	PMID[528597]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	2089.3	nM	PMID[528597]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	20653.8	nM	PMID[528597]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	4265.8	nM	PMID[528597]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	4064.43	nM	PMID[528597]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	2606.15	nM	PMID[528597]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1931.97	nM	PMID[528597]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	8729.71	nM	PMID[528597]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	7345.14	nM	PMID[528597]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	11194.38	nM	PMID[528597]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	21677.04	nM	PMID[528597]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	2624.22	nM	PMID[528597]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	1644.37	nM	PMID[528597]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	5888.44	nM	PMID[528597]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	4027.17	nM	PMID[528597]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	4581.42	nM	PMID[528597]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	4753.35	nM	PMID[528597]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	5035.01	nM	PMID[528597]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[528597]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	4187.94	nM	PMID[528597]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	31550.05	nM	PMID[528597]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	2477.42	nM	PMID[528597]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	2228.44	nM	PMID[528597]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	9794.9	nM	PMID[528597]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	19906.73	nM	PMID[528597]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	2570.4	nM	PMID[528597]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	5333.35	nM	PMID[528597]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	2344.23	nM	PMID[528597]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	23067.47	nM	PMID[528597]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	4808.39	nM	PMID[528597]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	2944.42	nM	PMID[528597]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	10739.89	nM	PMID[528597]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	1548.82	nM	PMID[528597]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	880.0	nM	PMID[528598]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4900.0	nM	PMID[528599]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	31000.0	nM	PMID[528602]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9100.0	nM	PMID[528602]
NPT398	Cell Line	UACC-62	Homo sapiens	IC50	=	2800.0	nM	PMID[528602]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	48000.0	nM	PMID[528602]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7000.0	nM	PMID[528602]
NPT169	Cell Line	B16-F10	Mus musculus	Activity	=	17.3	%	PMID[528602]
NPT169	Cell Line	B16-F10	Mus musculus	Activity	=	34.6	%	PMID[528602]
NPT169	Cell Line	B16-F10	Mus musculus	Activity	=	54.4	%	PMID[528602]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.95	ug.mL-1	PMID[528596]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.81	ug.mL-1	PMID[528596]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[528600]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28238.0	nM	PMID[528600]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	25.0	ug.mL-1	PMID[528601]
NPT23295	CELL-LINE	LNCaP C4-2B	Homo sapiens	IC50	=	4400.0	nM	PMID[528602]

☑ 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 NPC165608 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	312
0.1-0.2	2323
0.2-0.3	5867
0.3-0.4	12023
0.4-0.5	10888
0.5-0.6	6885
0.6-0.7	3933
0.7-0.8	438
0.8-0.85	20
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC477090
0.8641	High Similarity	NPC51719
0.8627	High Similarity	NPC474822
0.8571	High Similarity	NPC299590
0.8558	High Similarity	NPC122816
0.8476	Intermediate Similarity	NPC181994
0.8381	Intermediate Similarity	NPC471205
0.8333	Intermediate Similarity	NPC42658
0.8333	Intermediate Similarity	NPC16601
0.8333	Intermediate Similarity	NPC222834
0.8318	Intermediate Similarity	NPC177047
0.83	Intermediate Similarity	NPC471915
0.8257	Intermediate Similarity	NPC33360
0.8218	Intermediate Similarity	NPC475380
0.8218	Intermediate Similarity	NPC194132
0.8218	Intermediate Similarity	NPC209297
0.8208	Intermediate Similarity	NPC180744
0.82	Intermediate Similarity	NPC140277
0.8137	Intermediate Similarity	NPC199099
0.8137	Intermediate Similarity	NPC475446
0.8137	Intermediate Similarity	NPC311241
0.8137	Intermediate Similarity	NPC100912
0.81	Intermediate Similarity	NPC110022
0.81	Intermediate Similarity	NPC472640
0.81	Intermediate Similarity	NPC472641
0.8095	Intermediate Similarity	NPC281378
0.8095	Intermediate Similarity	NPC45897
0.8058	Intermediate Similarity	NPC107806
0.8058	Intermediate Similarity	NPC72647
0.8039	Intermediate Similarity	NPC260796
0.802	Intermediate Similarity	NPC161998
0.8019	Intermediate Similarity	NPC471937
0.8	Intermediate Similarity	NPC78594
0.8	Intermediate Similarity	NPC471914
0.8	Intermediate Similarity	NPC150228
0.8	Intermediate Similarity	NPC472552
0.8	Intermediate Similarity	NPC214005
0.7982	Intermediate Similarity	NPC253906
0.7965	Intermediate Similarity	NPC240509
0.7944	Intermediate Similarity	NPC471206
0.7941	Intermediate Similarity	NPC111273
0.7925	Intermediate Similarity	NPC471938
0.7925	Intermediate Similarity	NPC120009
0.7909	Intermediate Similarity	NPC469655
0.7909	Intermediate Similarity	NPC474846
0.7909	Intermediate Similarity	NPC469656
0.7905	Intermediate Similarity	NPC472554
0.79	Intermediate Similarity	NPC472642
0.789	Intermediate Similarity	NPC206618
0.789	Intermediate Similarity	NPC469370
0.7879	Intermediate Similarity	NPC93411
0.7876	Intermediate Similarity	NPC13713
0.7876	Intermediate Similarity	NPC58662
0.7845	Intermediate Similarity	NPC115349
0.783	Intermediate Similarity	NPC475038
0.783	Intermediate Similarity	NPC121423
0.783	Intermediate Similarity	NPC109195
0.781	Intermediate Similarity	NPC38855
0.781	Intermediate Similarity	NPC79303
0.781	Intermediate Similarity	NPC271295
0.7798	Intermediate Similarity	NPC38948
0.7798	Intermediate Similarity	NPC50124
0.7788	Intermediate Similarity	NPC232564
0.7788	Intermediate Similarity	NPC113425
0.7788	Intermediate Similarity	NPC471816
0.7788	Intermediate Similarity	NPC268213
0.7767	Intermediate Similarity	NPC276110
0.7757	Intermediate Similarity	NPC23584
0.7745	Intermediate Similarity	NPC7349
0.7739	Intermediate Similarity	NPC268326
0.7739	Intermediate Similarity	NPC153085
0.7736	Intermediate Similarity	NPC119467
0.7736	Intermediate Similarity	NPC475767
0.7736	Intermediate Similarity	NPC11974
0.7719	Intermediate Similarity	NPC290693
0.7706	Intermediate Similarity	NPC471601
0.7692	Intermediate Similarity	NPC8954
0.7692	Intermediate Similarity	NPC165632
0.7692	Intermediate Similarity	NPC94905
0.7685	Intermediate Similarity	NPC161775
0.7685	Intermediate Similarity	NPC477127
0.767	Intermediate Similarity	NPC105490
0.767	Intermediate Similarity	NPC477722
0.7664	Intermediate Similarity	NPC11956
0.7664	Intermediate Similarity	NPC165250
0.7653	Intermediate Similarity	NPC32223
0.7652	Intermediate Similarity	NPC83287
0.7642	Intermediate Similarity	NPC324841
0.7642	Intermediate Similarity	NPC188968
0.7642	Intermediate Similarity	NPC470761
0.7642	Intermediate Similarity	NPC473219
0.7636	Intermediate Similarity	NPC325054
0.7619	Intermediate Similarity	NPC51499
0.7615	Intermediate Similarity	NPC81630
0.76	Intermediate Similarity	NPC475087
0.7596	Intermediate Similarity	NPC476519
0.7593	Intermediate Similarity	NPC471208
0.7576	Intermediate Similarity	NPC253604
0.7576	Intermediate Similarity	NPC474013
0.7568	Intermediate Similarity	NPC475030
0.7568	Intermediate Similarity	NPC31522
0.7568	Intermediate Similarity	NPC257853
0.7565	Intermediate Similarity	NPC158344
0.7565	Intermediate Similarity	NPC77319
0.7565	Intermediate Similarity	NPC99728
0.7565	Intermediate Similarity	NPC50305
0.7565	Intermediate Similarity	NPC309034
0.7565	Intermediate Similarity	NPC244402
0.7565	Intermediate Similarity	NPC473852
0.7565	Intermediate Similarity	NPC142066
0.7565	Intermediate Similarity	NPC243196
0.7565	Intermediate Similarity	NPC471355
0.7565	Intermediate Similarity	NPC152615
0.7565	Intermediate Similarity	NPC471351
0.7565	Intermediate Similarity	NPC84987
0.7565	Intermediate Similarity	NPC471353
0.7565	Intermediate Similarity	NPC87250
0.7565	Intermediate Similarity	NPC27507
0.7565	Intermediate Similarity	NPC471354
0.7565	Intermediate Similarity	NPC34390
0.7565	Intermediate Similarity	NPC157376
0.7565	Intermediate Similarity	NPC196429
0.7565	Intermediate Similarity	NPC474418
0.7563	Intermediate Similarity	NPC469790
0.7547	Intermediate Similarity	NPC275086
0.7547	Intermediate Similarity	NPC325229
0.7545	Intermediate Similarity	NPC67321
0.7545	Intermediate Similarity	NPC187435
0.7545	Intermediate Similarity	NPC473586
0.7544	Intermediate Similarity	NPC471633
0.7544	Intermediate Similarity	NPC84949
0.7544	Intermediate Similarity	NPC69576
0.7544	Intermediate Similarity	NPC31354
0.7525	Intermediate Similarity	NPC242448
0.7523	Intermediate Similarity	NPC194941
0.7521	Intermediate Similarity	NPC475136
0.7521	Intermediate Similarity	NPC268530
0.7521	Intermediate Similarity	NPC154491
0.7521	Intermediate Similarity	NPC474466
0.7521	Intermediate Similarity	NPC251226
0.75	Intermediate Similarity	NPC476081
0.75	Intermediate Similarity	NPC472214
0.75	Intermediate Similarity	NPC295791
0.75	Intermediate Similarity	NPC472815
0.75	Intermediate Similarity	NPC472215
0.7478	Intermediate Similarity	NPC470793
0.7478	Intermediate Similarity	NPC199428
0.7478	Intermediate Similarity	NPC5311
0.7478	Intermediate Similarity	NPC193382
0.7478	Intermediate Similarity	NPC99620
0.7478	Intermediate Similarity	NPC310341
0.7477	Intermediate Similarity	NPC469916
0.7477	Intermediate Similarity	NPC475263
0.7477	Intermediate Similarity	NPC90946
0.7477	Intermediate Similarity	NPC300614
0.7477	Intermediate Similarity	NPC472439
0.7476	Intermediate Similarity	NPC329842
0.7458	Intermediate Similarity	NPC159456
0.7458	Intermediate Similarity	NPC204731
0.7458	Intermediate Similarity	NPC4021
0.7455	Intermediate Similarity	NPC220217
0.7455	Intermediate Similarity	NPC88349
0.7455	Intermediate Similarity	NPC119855
0.7453	Intermediate Similarity	NPC472188
0.7453	Intermediate Similarity	NPC474921
0.7453	Intermediate Similarity	NPC205143
0.7436	Intermediate Similarity	NPC470914
0.7436	Intermediate Similarity	NPC304260
0.7436	Intermediate Similarity	NPC29639
0.7436	Intermediate Similarity	NPC329905
0.7436	Intermediate Similarity	NPC44899
0.7436	Intermediate Similarity	NPC5883
0.7434	Intermediate Similarity	NPC194619
0.7434	Intermediate Similarity	NPC470076
0.7431	Intermediate Similarity	NPC159533
0.7431	Intermediate Similarity	NPC10232
0.7431	Intermediate Similarity	NPC189588
0.7431	Intermediate Similarity	NPC187302
0.7431	Intermediate Similarity	NPC97487
0.7431	Intermediate Similarity	NPC160583
0.7431	Intermediate Similarity	NPC474575
0.7431	Intermediate Similarity	NPC196471
0.7431	Intermediate Similarity	NPC472821
0.7429	Intermediate Similarity	NPC472189
0.7429	Intermediate Similarity	NPC472441
0.7429	Intermediate Similarity	NPC471362
0.7429	Intermediate Similarity	NPC471372
0.7414	Intermediate Similarity	NPC93883
0.7414	Intermediate Similarity	NPC203862
0.7414	Intermediate Similarity	NPC469684
0.7411	Intermediate Similarity	NPC475586
0.7411	Intermediate Similarity	NPC112457
0.7407	Intermediate Similarity	NPC198992
0.7407	Intermediate Similarity	NPC475617
0.7404	Intermediate Similarity	NPC163902
0.7395	Intermediate Similarity	NPC264336
0.7387	Intermediate Similarity	NPC475074
0.7387	Intermediate Similarity	NPC472820
0.7383	Intermediate Similarity	NPC222303
0.7383	Intermediate Similarity	NPC476800

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 NPC165608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	2448
0.2-0.3	3944
0.3-0.4	1687
0.4-0.5	499
0.5-0.6	236
0.6-0.7	40
0.7-0.8	6
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8738	High Similarity	NPD5954	Clinical (unspecified phase)
0.8571	High Similarity	NPD4061	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD7516	Approved
0.7652	Intermediate Similarity	NPD7327	Approved
0.7652	Intermediate Similarity	NPD7328	Approved
0.7642	Intermediate Similarity	NPD6648	Approved
0.757	Intermediate Similarity	NPD5344	Discontinued
0.7311	Intermediate Similarity	NPD8380	Approved
0.7311	Intermediate Similarity	NPD8379	Approved
0.7311	Intermediate Similarity	NPD8335	Approved
0.7311	Intermediate Similarity	NPD8296	Approved
0.7311	Intermediate Similarity	NPD8378	Approved
0.7311	Intermediate Similarity	NPD8033	Approved
0.7227	Intermediate Similarity	NPD8377	Approved
0.7227	Intermediate Similarity	NPD8294	Approved
0.7222	Intermediate Similarity	NPD7638	Approved
0.7168	Intermediate Similarity	NPD6686	Approved
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7073	Intermediate Similarity	NPD7507	Approved
0.704	Intermediate Similarity	NPD7319	Approved
0.7027	Intermediate Similarity	NPD7632	Discontinued
0.6909	Remote Similarity	NPD4225	Approved
0.6887	Remote Similarity	NPD3168	Discontinued
0.6842	Remote Similarity	NPD6008	Approved
0.6748	Remote Similarity	NPD7503	Approved
0.6694	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8133	Approved
0.6581	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4159	Approved
0.6423	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6009	Approved
0.6396	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7900	Approved
0.6356	Remote Similarity	NPD6412	Phase 2
0.633	Remote Similarity	NPD6051	Approved
0.6328	Remote Similarity	NPD7492	Approved
0.6308	Remote Similarity	NPD7736	Approved
0.6293	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6616	Approved
0.6273	Remote Similarity	NPD6698	Approved
0.6273	Remote Similarity	NPD46	Approved
0.6273	Remote Similarity	NPD7838	Discovery
0.627	Remote Similarity	NPD6054	Approved
0.627	Remote Similarity	NPD6059	Approved
0.6262	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD8328	Phase 3
0.6231	Remote Similarity	NPD8293	Discontinued
0.6231	Remote Similarity	NPD7078	Approved
0.623	Remote Similarity	NPD6882	Approved
0.6228	Remote Similarity	NPD7902	Approved
0.622	Remote Similarity	NPD6016	Approved
0.622	Remote Similarity	NPD6015	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6174	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5988	Approved
0.6172	Remote Similarity	NPD6370	Approved
0.6142	Remote Similarity	NPD6319	Approved
0.6134	Remote Similarity	NPD6675	Approved
0.6134	Remote Similarity	NPD5739	Approved
0.6134	Remote Similarity	NPD7128	Approved
0.6134	Remote Similarity	NPD6402	Approved
0.6134	Remote Similarity	NPD5357	Phase 1
0.6098	Remote Similarity	NPD8297	Approved
0.6091	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5697	Approved
0.6083	Remote Similarity	NPD5701	Approved
0.6071	Remote Similarity	NPD5693	Phase 1
0.6071	Remote Similarity	NPD7515	Phase 2
0.6055	Remote Similarity	NPD7146	Approved
0.6055	Remote Similarity	NPD7334	Approved
0.6055	Remote Similarity	NPD6409	Approved
0.6055	Remote Similarity	NPD5330	Approved
0.6055	Remote Similarity	NPD6684	Approved
0.6055	Remote Similarity	NPD7521	Approved
0.6053	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD7320	Approved
0.6033	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6399	Phase 3
0.6014	Remote Similarity	NPD7625	Phase 1
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.5984	Remote Similarity	NPD6014	Approved
0.5984	Remote Similarity	NPD6372	Approved
0.5984	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD6013	Approved
0.5984	Remote Similarity	NPD6373	Approved
0.5969	Remote Similarity	NPD8517	Approved
0.5969	Remote Similarity	NPD5983	Phase 2
0.5969	Remote Similarity	NPD8513	Phase 3
0.5969	Remote Similarity	NPD6921	Approved
0.5969	Remote Similarity	NPD8515	Approved
0.5969	Remote Similarity	NPD8516	Approved
0.5968	Remote Similarity	NPD6053	Discontinued
0.5965	Remote Similarity	NPD6001	Approved
0.5963	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6672	Approved
0.5946	Remote Similarity	NPD5737	Approved
0.5946	Remote Similarity	NPD6903	Approved
0.5943	Remote Similarity	NPD7525	Registered
0.5935	Remote Similarity	NPD7290	Approved
0.5935	Remote Similarity	NPD7102	Approved
0.5935	Remote Similarity	NPD6371	Approved
0.5935	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD8035	Phase 2
0.5929	Remote Similarity	NPD7637	Suspended
0.5929	Remote Similarity	NPD8034	Phase 2
0.5902	Remote Similarity	NPD6011	Approved
0.5893	Remote Similarity	NPD1695	Approved
0.5887	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD8130	Phase 1
0.5887	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6847	Approved
0.5887	Remote Similarity	NPD6649	Approved
0.5887	Remote Similarity	NPD6869	Approved
0.5887	Remote Similarity	NPD6650	Approved
0.5878	Remote Similarity	NPD6067	Discontinued
0.5872	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6033	Approved
0.5816	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6084	Phase 2
0.5812	Remote Similarity	NPD6083	Phase 2
0.5812	Remote Similarity	NPD4755	Approved
0.5789	Remote Similarity	NPD6336	Discontinued
0.578	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.578	Remote Similarity	NPD3669	Approved
0.578	Remote Similarity	NPD6695	Phase 3
0.5776	Remote Similarity	NPD5695	Phase 3
0.5766	Remote Similarity	NPD3618	Phase 1
0.5763	Remote Similarity	NPD5696	Approved
0.576	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6080	Approved
0.5752	Remote Similarity	NPD6904	Approved
0.5752	Remote Similarity	NPD6673	Approved
0.575	Remote Similarity	NPD5211	Phase 2
0.5746	Remote Similarity	NPD8074	Phase 3
0.5741	Remote Similarity	NPD1779	Approved
0.5741	Remote Similarity	NPD1780	Approved
0.5739	Remote Similarity	NPD4202	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5703	Remote Similarity	NPD6274	Approved
0.5701	Remote Similarity	NPD7645	Phase 2
0.5691	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD2686	Approved
0.5686	Remote Similarity	NPD2254	Approved
0.5686	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD2687	Approved
0.568	Remote Similarity	NPD4634	Approved
0.5676	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD1700	Approved
0.5664	Remote Similarity	NPD5208	Approved
0.5656	Remote Similarity	NPD5141	Approved
0.562	Remote Similarity	NPD5225	Approved
0.562	Remote Similarity	NPD5226	Approved
0.562	Remote Similarity	NPD4633	Approved
0.562	Remote Similarity	NPD5224	Approved
0.5614	Remote Similarity	NPD5328	Approved
0.5607	Remote Similarity	NPD6115	Approved
0.5607	Remote Similarity	NPD6118	Approved
0.5607	Remote Similarity	NPD6697	Approved
0.5607	Remote Similarity	NPD6114	Approved

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