NPASS Compound

Structure

CID123194 OpenBabel06191715482D 32 35 0 0 1 0 0 0 0 0999 V2000 1.4605 -5.8867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9999 -5.2008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6685 -4.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 -3.2204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0912 1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3744 2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2482 2.4517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5304 -0.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2079 -3.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8119 -2.5346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8439 1.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2166 0.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6861 -0.9729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 -0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3735 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6859 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8431 -1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0322 -5.0994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6362 -4.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 -2.4331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2169 1.4598 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8439 -1.4601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6870 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8437 0.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5310 1.4602 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3741 1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5307 0.4863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9734 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 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 2 0 0 0 0 6 29 1 0 0 0 0 7 29 1 0 0 0 0 9 31 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 30 1 0 0 0 0 19 32 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 23 4 1 1 0 0 0 23 25 1 0 0 0 0 24 5 1 6 0 0 0 24 29 1 0 0 0 0 25 31 1 6 0 0 0 26 27 2 0 0 0 0 26 30 1 0 0 0 0 27 32 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 30 8 1 6 0 0 0 31 32 1 6 0 0 0 32 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.42
Volume:	522.529
LogP:	8.733
LogD:	6.887
LogS:	-7.383
# Rotatable Bonds:	5
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.683
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	8.135481039062142e-06
Pgp-inhibitor:	0.679
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	94.0776138305664%
Volume Distribution (VD):	2.497
Pgp-substrate:	1.5847185850143433%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.576
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.984
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.622
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.888

ADMET: Excretion

Clearance (CL):	6.296
Half-life (T1/2):	0.008

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.346
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.319
Skin Sensitization:	0.116
Carcinogencity:	0.019
Eye Corrosion:	0.907
Eye Irritation:	0.893
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC123194

Natural Product ID:	NPC123194
*Common Name:**	Eburicol
IUPAC Name:	(3S,10S,13R,14R,17R)-3,4,4,10,13,14-hexamethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene
Synonyms:	Eburicol
Standard InCHIKey:	KBHVSNYZPRMDBJ-PCBLTFNCSA-N
Standard InCHI:	InChI=1S/C32H54/c1-21(2)22(3)11-12-23(4)25-16-19-32(10)27-13-14-28-29(6,7)24(5)15-18-30(28,8)26(27)17-20-31(25,32)9/h21,23-25,28H,3,11-20H2,1-2,4-10H3/t23-,24+,25-,28?,30-,31-,32+/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CCC2[C@]1(C)CC[C@@H](C2(C)C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426367
PubChem CID:	44424396
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]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
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]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3354	Fomes officinalis	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]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	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]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
EC50	2
IC50	5
Others	4

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	3
Others	2
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	22300.0	nM	PMID[460134]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	20000.0	nM	PMID[460135]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	34.0	%	PMID[460135]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	22300.0	nM	PMID[460135]
NPT2	Others	Unspecified		IC50	=	50470.0	nM	PMID[460133]
NPT2	Others	Unspecified		IC50	=	21900.0	nM	PMID[460134]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	20000.0	nM	PMID[460135]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	18.0	%	PMID[460135]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21900.0	nM	PMID[460135]
NPT23766	SINGLE PROTEIN	14-alpha sterol demethylase	Neosartorya fumigata	Ks	=	22.6	uM	PMID[460136]
NPT23766	SINGLE PROTEIN	14-alpha sterol demethylase	Neosartorya fumigata	Ks	=	4.1	uM	PMID[460136]

☑ 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 NPC123194 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	601
0.1-0.2	8121
0.2-0.3	18042
0.3-0.4	8321
0.4-0.5	5476
0.5-0.6	1768
0.6-0.7	332
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC469769
0.8462	Intermediate Similarity	NPC17518
0.8214	Intermediate Similarity	NPC470893
0.8182	Intermediate Similarity	NPC127944
0.8113	Intermediate Similarity	NPC22765
0.7963	Intermediate Similarity	NPC200129
0.7925	Intermediate Similarity	NPC124851
0.7895	Intermediate Similarity	NPC469770
0.7885	Intermediate Similarity	NPC86683
0.7885	Intermediate Similarity	NPC49088
0.7843	Intermediate Similarity	NPC192529
0.7736	Intermediate Similarity	NPC323445
0.7692	Intermediate Similarity	NPC202189
0.7656	Intermediate Similarity	NPC176107
0.7538	Intermediate Similarity	NPC20610
0.75	Intermediate Similarity	NPC92327
0.7455	Intermediate Similarity	NPC17810
0.7424	Intermediate Similarity	NPC182815
0.7353	Intermediate Similarity	NPC470044
0.7353	Intermediate Similarity	NPC470045
0.7333	Intermediate Similarity	NPC475696
0.7333	Intermediate Similarity	NPC474528
0.7333	Intermediate Similarity	NPC474415
0.7313	Intermediate Similarity	NPC35734
0.7313	Intermediate Similarity	NPC282593
0.7313	Intermediate Similarity	NPC475728
0.7313	Intermediate Similarity	NPC159577
0.7308	Intermediate Similarity	NPC193180
0.7302	Intermediate Similarity	NPC474086
0.7246	Intermediate Similarity	NPC476904
0.7231	Intermediate Similarity	NPC176171
0.7222	Intermediate Similarity	NPC241784
0.7222	Intermediate Similarity	NPC13991
0.7222	Intermediate Similarity	NPC114239
0.7222	Intermediate Similarity	NPC296337
0.7206	Intermediate Similarity	NPC115023
0.7206	Intermediate Similarity	NPC470078
0.7206	Intermediate Similarity	NPC21773
0.717	Intermediate Similarity	NPC141777
0.717	Intermediate Similarity	NPC227670
0.717	Intermediate Similarity	NPC166362
0.7143	Intermediate Similarity	NPC471468
0.7143	Intermediate Similarity	NPC121744
0.7143	Intermediate Similarity	NPC118508
0.7143	Intermediate Similarity	NPC322353
0.7115	Intermediate Similarity	NPC103290
0.7101	Intermediate Similarity	NPC251705
0.7101	Intermediate Similarity	NPC303613
0.7101	Intermediate Similarity	NPC474228
0.7097	Intermediate Similarity	NPC475716
0.7097	Intermediate Similarity	NPC474420
0.7097	Intermediate Similarity	NPC474454
0.7097	Intermediate Similarity	NPC474455
0.7059	Intermediate Similarity	NPC477856
0.7059	Intermediate Similarity	NPC307176
0.7059	Intermediate Similarity	NPC214770
0.7049	Intermediate Similarity	NPC474457
0.7042	Intermediate Similarity	NPC202642
0.7042	Intermediate Similarity	NPC46160
0.7042	Intermediate Similarity	NPC73875
0.7042	Intermediate Similarity	NPC470362
0.7037	Intermediate Similarity	NPC248411
0.7015	Intermediate Similarity	NPC160209
0.6981	Remote Similarity	NPC190232
0.6981	Remote Similarity	NPC105246
0.697	Remote Similarity	NPC323005
0.6957	Remote Similarity	NPC223187
0.6957	Remote Similarity	NPC234707
0.6957	Remote Similarity	NPC265789
0.6944	Remote Similarity	NPC475027
0.6944	Remote Similarity	NPC214570
0.6912	Remote Similarity	NPC139397
0.6909	Remote Similarity	NPC229403
0.6901	Remote Similarity	NPC28657
0.6901	Remote Similarity	NPC134847
0.6901	Remote Similarity	NPC288035
0.6901	Remote Similarity	NPC257347
0.6901	Remote Similarity	NPC285893
0.6901	Remote Similarity	NPC230301
0.6901	Remote Similarity	NPC162742
0.6901	Remote Similarity	NPC304309
0.6901	Remote Similarity	NPC141071
0.6901	Remote Similarity	NPC136188
0.6901	Remote Similarity	NPC293803
0.6901	Remote Similarity	NPC471723
0.6901	Remote Similarity	NPC22105
0.6857	Remote Similarity	NPC474140
0.6857	Remote Similarity	NPC201373
0.6849	Remote Similarity	NPC275910
0.6849	Remote Similarity	NPC469996
0.6849	Remote Similarity	NPC205455
0.6849	Remote Similarity	NPC186191
0.6825	Remote Similarity	NPC309825
0.6818	Remote Similarity	NPC163678
0.6812	Remote Similarity	NPC2634
0.6812	Remote Similarity	NPC265782
0.6812	Remote Similarity	NPC40574
0.6812	Remote Similarity	NPC260040
0.6812	Remote Similarity	NPC251929
0.6806	Remote Similarity	NPC134330
0.6806	Remote Similarity	NPC107059
0.6806	Remote Similarity	NPC7214
0.6806	Remote Similarity	NPC300324
0.6806	Remote Similarity	NPC474463
0.6806	Remote Similarity	NPC321381
0.6806	Remote Similarity	NPC321016
0.6806	Remote Similarity	NPC240604
0.6806	Remote Similarity	NPC244488
0.6806	Remote Similarity	NPC189883
0.6806	Remote Similarity	NPC69408
0.6806	Remote Similarity	NPC247325
0.6806	Remote Similarity	NPC113733
0.6806	Remote Similarity	NPC129165
0.678	Remote Similarity	NPC473728
0.6765	Remote Similarity	NPC216460
0.6761	Remote Similarity	NPC309852
0.6761	Remote Similarity	NPC255021
0.6757	Remote Similarity	NPC170793
0.6757	Remote Similarity	NPC90965
0.6716	Remote Similarity	NPC286669
0.6716	Remote Similarity	NPC107704
0.6716	Remote Similarity	NPC43300
0.6716	Remote Similarity	NPC189917
0.6716	Remote Similarity	NPC222366
0.6716	Remote Similarity	NPC168824
0.6716	Remote Similarity	NPC96812
0.6716	Remote Similarity	NPC39462
0.6716	Remote Similarity	NPC476039
0.6714	Remote Similarity	NPC305501
0.6714	Remote Similarity	NPC54123
0.6712	Remote Similarity	NPC318495
0.6712	Remote Similarity	NPC155986
0.6712	Remote Similarity	NPC475025
0.6712	Remote Similarity	NPC34019
0.6712	Remote Similarity	NPC198968
0.6667	Remote Similarity	NPC474416
0.6667	Remote Similarity	NPC469662
0.6667	Remote Similarity	NPC178644
0.6667	Remote Similarity	NPC473912
0.6667	Remote Similarity	NPC125828
0.6622	Remote Similarity	NPC477514
0.6622	Remote Similarity	NPC474216
0.6622	Remote Similarity	NPC105197
0.6622	Remote Similarity	NPC473943
0.6622	Remote Similarity	NPC82635
0.6622	Remote Similarity	NPC475337
0.6622	Remote Similarity	NPC18603
0.6622	Remote Similarity	NPC318136
0.6622	Remote Similarity	NPC307965
0.6622	Remote Similarity	NPC87604
0.6622	Remote Similarity	NPC76931
0.6622	Remote Similarity	NPC470052
0.6622	Remote Similarity	NPC477522
0.6618	Remote Similarity	NPC193770
0.6618	Remote Similarity	NPC197805
0.6615	Remote Similarity	NPC469728
0.6604	Remote Similarity	NPC227632
0.6604	Remote Similarity	NPC246165
0.6604	Remote Similarity	NPC62086
0.6604	Remote Similarity	NPC78551
0.6579	Remote Similarity	NPC201912
0.6579	Remote Similarity	NPC38350
0.6579	Remote Similarity	NPC4166
0.6579	Remote Similarity	NPC474122
0.6575	Remote Similarity	NPC237460
0.6575	Remote Similarity	NPC474231
0.6567	Remote Similarity	NPC476737
0.6567	Remote Similarity	NPC27243
0.6545	Remote Similarity	NPC474118
0.6545	Remote Similarity	NPC90803
0.6545	Remote Similarity	NPC90506
0.6545	Remote Similarity	NPC23145
0.6545	Remote Similarity	NPC51762
0.6538	Remote Similarity	NPC297643
0.6538	Remote Similarity	NPC139717
0.6538	Remote Similarity	NPC229262
0.6533	Remote Similarity	NPC143182
0.6533	Remote Similarity	NPC47982
0.6533	Remote Similarity	NPC44083
0.6533	Remote Similarity	NPC109546
0.6533	Remote Similarity	NPC209430
0.6533	Remote Similarity	NPC28862
0.6533	Remote Similarity	NPC84694
0.6533	Remote Similarity	NPC190211
0.6533	Remote Similarity	NPC1319
0.6533	Remote Similarity	NPC81306
0.6533	Remote Similarity	NPC153987
0.6533	Remote Similarity	NPC30986
0.6533	Remote Similarity	NPC328714
0.6528	Remote Similarity	NPC469593
0.6528	Remote Similarity	NPC469533
0.6528	Remote Similarity	NPC469534
0.6522	Remote Similarity	NPC188292
0.6522	Remote Similarity	NPC82477
0.6522	Remote Similarity	NPC142754
0.6522	Remote Similarity	NPC310992
0.6522	Remote Similarity	NPC296697
0.6522	Remote Similarity	NPC39157
0.6522	Remote Similarity	NPC260474
0.6522	Remote Similarity	NPC476945

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 NPC123194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	532
0.1-0.2	4330
0.2-0.3	3288
0.3-0.4	639
0.4-0.5	221
0.5-0.6	104
0.6-0.7	29
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7455	Intermediate Similarity	NPD8262	Approved
0.7313	Intermediate Similarity	NPD6938	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6939	Phase 2
0.7246	Intermediate Similarity	NPD5733	Approved
0.7206	Intermediate Similarity	NPD4243	Approved
0.7059	Intermediate Similarity	NPD4747	Approved
0.7015	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4784	Approved
0.7	Intermediate Similarity	NPD4785	Approved
0.7	Intermediate Similarity	NPD4687	Approved
0.6981	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5276	Approved
0.6912	Remote Similarity	NPD4137	Phase 3
0.6901	Remote Similarity	NPD7339	Approved
0.6901	Remote Similarity	NPD6942	Approved
0.6812	Remote Similarity	NPD4691	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD5275	Approved
0.6528	Remote Similarity	NPD4058	Approved
0.6429	Remote Similarity	NPD6922	Approved
0.6429	Remote Similarity	NPD6923	Approved
0.6351	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD319	Phase 1
0.6338	Remote Similarity	NPD7144	Approved
0.6338	Remote Similarity	NPD7143	Approved
0.6316	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD7151	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD7152	Approved
0.6234	Remote Similarity	NPD7525	Registered
0.6125	Remote Similarity	NPD4786	Approved
0.6081	Remote Similarity	NPD6926	Approved
0.6081	Remote Similarity	NPD6924	Approved
0.6076	Remote Similarity	NPD4223	Phase 3
0.6076	Remote Similarity	NPD4221	Approved
0.6049	Remote Similarity	NPD5329	Approved
0.6026	Remote Similarity	NPD4748	Discontinued
0.6	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4694	Approved
0.5976	Remote Similarity	NPD6098	Approved
0.5976	Remote Similarity	NPD5280	Approved
0.5976	Remote Similarity	NPD5690	Phase 2
0.5949	Remote Similarity	NPD4692	Approved
0.5949	Remote Similarity	NPD4139	Approved
0.5926	Remote Similarity	NPD4197	Approved
0.5921	Remote Similarity	NPD6933	Approved
0.5875	Remote Similarity	NPD3667	Approved
0.5844	Remote Similarity	NPD5776	Phase 2
0.5844	Remote Similarity	NPD6925	Approved
0.5844	Remote Similarity	NPD6932	Approved
0.5833	Remote Similarity	NPD5737	Approved
0.5833	Remote Similarity	NPD6672	Approved
0.5814	Remote Similarity	NPD6050	Approved
0.5789	Remote Similarity	NPD8264	Approved
0.5783	Remote Similarity	NPD4689	Approved
0.5783	Remote Similarity	NPD7146	Approved
0.5783	Remote Similarity	NPD4690	Approved
0.5783	Remote Similarity	NPD6684	Approved
0.5783	Remote Similarity	NPD5205	Approved
0.5783	Remote Similarity	NPD4138	Approved
0.5783	Remote Similarity	NPD5330	Approved
0.5783	Remote Similarity	NPD4688	Approved
0.5783	Remote Similarity	NPD7521	Approved
0.5783	Remote Similarity	NPD5279	Phase 3
0.5783	Remote Similarity	NPD4693	Phase 3
0.5783	Remote Similarity	NPD6409	Approved
0.5783	Remote Similarity	NPD7334	Approved
0.5769	Remote Similarity	NPD7145	Approved
0.5769	Remote Similarity	NPD3617	Approved
0.5765	Remote Similarity	NPD5328	Approved
0.5765	Remote Similarity	NPD6904	Approved
0.5765	Remote Similarity	NPD6051	Approved
0.5765	Remote Similarity	NPD6080	Approved
0.5765	Remote Similarity	NPD6673	Approved
0.575	Remote Similarity	NPD8028	Phase 2
0.5732	Remote Similarity	NPD3666	Approved
0.5732	Remote Similarity	NPD3665	Phase 1
0.5732	Remote Similarity	NPD3133	Approved
0.5732	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5207	Approved
0.5698	Remote Similarity	NPD5692	Phase 3
0.5696	Remote Similarity	NPD7645	Phase 2
0.5696	Remote Similarity	NPD6683	Phase 2
0.5696	Remote Similarity	NPD6929	Approved
0.5672	Remote Similarity	NPD287	Approved
0.5647	Remote Similarity	NPD4723	Approved
0.5647	Remote Similarity	NPD4722	Approved
0.5647	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD6903	Approved
0.5647	Remote Similarity	NPD5208	Approved
0.5632	Remote Similarity	NPD5694	Approved
0.5632	Remote Similarity	NPD5284	Approved
0.5632	Remote Similarity	NPD5281	Approved
0.5632	Remote Similarity	NPD6079	Approved
0.5625	Remote Similarity	NPD6931	Approved
0.5625	Remote Similarity	NPD7514	Phase 3
0.5625	Remote Similarity	NPD6930	Phase 2
0.5606	Remote Similarity	NPD4219	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