NPASS Compound

Structure

CID127944 OpenBabel06191715482D 30 34 0 0 1 0 0 0 0 0999 V2000 2.7227 -3.6002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2179 -2.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4372 1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9465 0.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4577 0.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0240 1.9062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8672 -1.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6388 2.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6383 0.9465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8189 1.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0957 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6391 -1.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6374 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4574 2.3634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8197 2.3643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0954 -0.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8197 -1.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8186 -0.4732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2780 -2.8355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2777 -1.8905 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4583 -1.4177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6377 0.9455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6386 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9460 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4568 1.4178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4580 -0.4723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8191 1.4188 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8194 -0.4728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 21 20 1 6 0 0 0 21 22 1 0 0 0 0 22 27 1 6 0 0 0 23 26 1 0 0 0 0 23 28 1 1 0 0 0 24 27 1 6 0 0 0 24 29 1 0 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.39
Volume:	482.017
LogP:	8.368
LogD:	5.951
LogS:	-7.338
# Rotatable Bonds:	1
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	4.544
Fsp3:	0.933
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:	-4.925
MDCK Permeability:	7.402957635349594e-06
Pgp-inhibitor:	0.166
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	96.39151000976562%
Volume Distribution (VD):	2.526
Pgp-substrate:	1.8323708772659302%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.52
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.583

ADMET: Excretion

Clearance (CL):	6.935
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.951
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.162
Skin Sensitization:	0.952
Carcinogencity:	0.105
Eye Corrosion:	0.995
Eye Irritation:	0.855
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC127944

Natural Product ID:	NPC127944
*Common Name:**	Hop-22(29)-Ene
IUPAC Name:	(3S,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-3-prop-1-en-2-yl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysene
Synonyms:
Standard InCHIKey:	HHXYJYBYNZMZKX-PYQRSULMSA-N
Standard InCHI:	InChI=1S/C30H50/c1-20(2)21-12-17-27(5)22(21)13-18-29(7)24(27)10-11-25-28(6)16-9-15-26(3,4)23(28)14-19-30(25,29)8/h21-25H,1,9-19H2,2-8H3/t21-,22+,23+,24-,25-,27+,28+,29-,30-/m1/s1
SMILES:	CC(=C)[C@H]1CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CCCC1(C)C)C)C
Synthetic Gene Cluster:	BGC0000663;
ChEMBL Identifier:	CHEMBL455613
PubChem CID:	92155
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids

*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
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)80275-7]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[12951487]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16870425]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377852]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24013342]
NPO29331	Pyrrosia sheareri	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1639	Pyrrosia lingua	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29331	Pyrrosia sheareri	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1639	Pyrrosia lingua	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29331	Pyrrosia sheareri	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1639	Pyrrosia lingua	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1639	Pyrrosia lingua	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29331	Pyrrosia sheareri	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3590	Acanthus mollis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29331	Pyrrosia sheareri	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5238	Salvia pubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4529	Gomphidius rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1639	Pyrrosia lingua	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13678	Melicope sessiliflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6490	Chromolaena laevigata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12550	Mikania decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO282	Crepis pulchra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14586	Baccharis crispa	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1887	Organism	Phytophthora cactorum	Phytophthora cactorum	Activity	=	30.0	mm	PMID[532234]

☑ 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 NPC127944 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	736
0.1-0.2	12757
0.2-0.3	15295
0.3-0.4	6366
0.4-0.5	5182
0.5-0.6	1997
0.6-0.7	327
0.7-0.8	34
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC469770
0.8182	Intermediate Similarity	NPC123194
0.8033	Intermediate Similarity	NPC43300
0.7959	Intermediate Similarity	NPC193180
0.7759	Intermediate Similarity	NPC469769
0.7755	Intermediate Similarity	NPC103290
0.7736	Intermediate Similarity	NPC22765
0.75	Intermediate Similarity	NPC474416
0.746	Intermediate Similarity	NPC39462
0.746	Intermediate Similarity	NPC168824
0.746	Intermediate Similarity	NPC189917
0.746	Intermediate Similarity	NPC107704
0.746	Intermediate Similarity	NPC96812
0.7451	Intermediate Similarity	NPC141777
0.7451	Intermediate Similarity	NPC227670
0.7451	Intermediate Similarity	NPC166362
0.7407	Intermediate Similarity	NPC17518
0.7302	Intermediate Similarity	NPC476737
0.7302	Intermediate Similarity	NPC27243
0.7255	Intermediate Similarity	NPC105246
0.7255	Intermediate Similarity	NPC190232
0.7222	Intermediate Similarity	NPC124851
0.7206	Intermediate Similarity	NPC192638
0.7206	Intermediate Similarity	NPC159497
0.7206	Intermediate Similarity	NPC62657
0.7206	Intermediate Similarity	NPC25511
0.717	Intermediate Similarity	NPC229403
0.717	Intermediate Similarity	NPC49088
0.7121	Intermediate Similarity	NPC477857
0.7101	Intermediate Similarity	NPC212879
0.7101	Intermediate Similarity	NPC240235
0.7101	Intermediate Similarity	NPC178383
0.7101	Intermediate Similarity	NPC104387
0.7101	Intermediate Similarity	NPC231256
0.7077	Intermediate Similarity	NPC176107
0.7049	Intermediate Similarity	NPC474455
0.7049	Intermediate Similarity	NPC474420
0.7049	Intermediate Similarity	NPC474454
0.7037	Intermediate Similarity	NPC323445
0.7015	Intermediate Similarity	NPC477856
0.7015	Intermediate Similarity	NPC214770
0.7	Intermediate Similarity	NPC14112
0.7	Intermediate Similarity	NPC278091
0.7	Intermediate Similarity	NPC93662
0.7	Intermediate Similarity	NPC86305
0.7	Intermediate Similarity	NPC474457
0.7	Intermediate Similarity	NPC78067
0.6984	Remote Similarity	NPC474086
0.697	Remote Similarity	NPC20610
0.6964	Remote Similarity	NPC476681
0.6964	Remote Similarity	NPC200129
0.6949	Remote Similarity	NPC470893
0.6923	Remote Similarity	NPC92327
0.6912	Remote Similarity	NPC111234
0.6901	Remote Similarity	NPC202540
0.6901	Remote Similarity	NPC119355
0.6901	Remote Similarity	NPC68828
0.6901	Remote Similarity	NPC248830
0.6901	Remote Similarity	NPC212241
0.6866	Remote Similarity	NPC182815
0.6863	Remote Similarity	NPC246165
0.6863	Remote Similarity	NPC227632
0.6863	Remote Similarity	NPC62086
0.6863	Remote Similarity	NPC78551
0.6857	Remote Similarity	NPC293803
0.6852	Remote Similarity	NPC86683
0.6812	Remote Similarity	NPC195489
0.6806	Remote Similarity	NPC42853
0.6806	Remote Similarity	NPC102708
0.6806	Remote Similarity	NPC63020
0.6792	Remote Similarity	NPC51762
0.6792	Remote Similarity	NPC23145
0.6792	Remote Similarity	NPC90506
0.6792	Remote Similarity	NPC90803
0.6792	Remote Similarity	NPC474118
0.6792	Remote Similarity	NPC192529
0.6765	Remote Similarity	NPC45296
0.6765	Remote Similarity	NPC40574
0.6765	Remote Similarity	NPC475728
0.6765	Remote Similarity	NPC159577
0.6765	Remote Similarity	NPC35734
0.6765	Remote Similarity	NPC282593
0.6721	Remote Similarity	NPC474415
0.6721	Remote Similarity	NPC173815
0.6721	Remote Similarity	NPC475696
0.6721	Remote Similarity	NPC474528
0.6716	Remote Similarity	NPC82477
0.6716	Remote Similarity	NPC142754
0.6716	Remote Similarity	NPC296697
0.6716	Remote Similarity	NPC39157
0.6716	Remote Similarity	NPC160209
0.6714	Remote Similarity	NPC254509
0.6714	Remote Similarity	NPC5046
0.6714	Remote Similarity	NPC49168
0.6714	Remote Similarity	NPC196358
0.6714	Remote Similarity	NPC145552
0.6712	Remote Similarity	NPC472742
0.6712	Remote Similarity	NPC475727
0.6712	Remote Similarity	NPC49599
0.6712	Remote Similarity	NPC80297
0.6712	Remote Similarity	NPC192744
0.6712	Remote Similarity	NPC305835
0.6712	Remote Similarity	NPC116119
0.6712	Remote Similarity	NPC49627
0.6712	Remote Similarity	NPC201459
0.6667	Remote Similarity	NPC115023
0.6667	Remote Similarity	NPC470078
0.6667	Remote Similarity	NPC164045
0.6667	Remote Similarity	NPC21773
0.6622	Remote Similarity	NPC475679
0.6622	Remote Similarity	NPC304194
0.662	Remote Similarity	NPC185536
0.662	Remote Similarity	NPC200243
0.662	Remote Similarity	NPC70982
0.662	Remote Similarity	NPC3403
0.662	Remote Similarity	NPC230704
0.6618	Remote Similarity	NPC286814
0.6613	Remote Similarity	NPC162685
0.6613	Remote Similarity	NPC324944
0.6571	Remote Similarity	NPC279241
0.6571	Remote Similarity	NPC303613
0.6571	Remote Similarity	NPC474228
0.6571	Remote Similarity	NPC251705
0.6571	Remote Similarity	NPC472506
0.6567	Remote Similarity	NPC20181
0.6567	Remote Similarity	NPC220210
0.6557	Remote Similarity	NPC318036
0.6533	Remote Similarity	NPC103754
0.6533	Remote Similarity	NPC474484
0.6528	Remote Similarity	NPC246445
0.6528	Remote Similarity	NPC91573
0.6528	Remote Similarity	NPC237460
0.6522	Remote Similarity	NPC307176
0.6508	Remote Similarity	NPC475716
0.65	Remote Similarity	NPC476683
0.6479	Remote Similarity	NPC472503
0.6479	Remote Similarity	NPC476736
0.6479	Remote Similarity	NPC308440
0.6479	Remote Similarity	NPC476904
0.6438	Remote Similarity	NPC91665
0.6438	Remote Similarity	NPC66105
0.6438	Remote Similarity	NPC331618
0.6438	Remote Similarity	NPC474230
0.6438	Remote Similarity	NPC257191
0.6429	Remote Similarity	NPC265789
0.6429	Remote Similarity	NPC301226
0.6429	Remote Similarity	NPC190035
0.6429	Remote Similarity	NPC234707
0.6418	Remote Similarity	NPC176171
0.6418	Remote Similarity	NPC474456
0.6418	Remote Similarity	NPC323005
0.6415	Remote Similarity	NPC473614
0.64	Remote Similarity	NPC474509
0.6393	Remote Similarity	NPC184819
0.6389	Remote Similarity	NPC28657
0.6389	Remote Similarity	NPC304309
0.6389	Remote Similarity	NPC471723
0.6389	Remote Similarity	NPC141071
0.6389	Remote Similarity	NPC134847
0.6389	Remote Similarity	NPC255650
0.6389	Remote Similarity	NPC103822
0.6389	Remote Similarity	NPC162742
0.6389	Remote Similarity	NPC288035
0.6389	Remote Similarity	NPC136188
0.6389	Remote Similarity	NPC22105
0.6389	Remote Similarity	NPC257347
0.6389	Remote Similarity	NPC230301
0.6389	Remote Similarity	NPC285893
0.6377	Remote Similarity	NPC139397
0.6364	Remote Similarity	NPC246956
0.6364	Remote Similarity	NPC175410
0.6364	Remote Similarity	NPC5280
0.6364	Remote Similarity	NPC472743
0.6364	Remote Similarity	NPC472740
0.6364	Remote Similarity	NPC475726
0.6364	Remote Similarity	NPC202189
0.6364	Remote Similarity	NPC473742
0.6351	Remote Similarity	NPC477819
0.6351	Remote Similarity	NPC302041
0.6351	Remote Similarity	NPC167037
0.6351	Remote Similarity	NPC31828
0.6351	Remote Similarity	NPC6978
0.6351	Remote Similarity	NPC477817
0.6351	Remote Similarity	NPC285761
0.6351	Remote Similarity	NPC244385
0.6351	Remote Similarity	NPC85346
0.6351	Remote Similarity	NPC138621
0.6351	Remote Similarity	NPC472342
0.6351	Remote Similarity	NPC301707
0.6351	Remote Similarity	NPC65897
0.6338	Remote Similarity	NPC36310
0.6338	Remote Similarity	NPC211009
0.6338	Remote Similarity	NPC470044
0.6338	Remote Similarity	NPC470045
0.6338	Remote Similarity	NPC161187
0.6338	Remote Similarity	NPC244708
0.6338	Remote Similarity	NPC474743
0.6338	Remote Similarity	NPC330659
0.6338	Remote Similarity	NPC474488
0.6308	Remote Similarity	NPC147524

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 NPC127944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	623
0.1-0.2	5190
0.2-0.3	2579
0.3-0.4	408
0.4-0.5	227
0.5-0.6	105
0.6-0.7	18
0.7-0.8	0
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
0.7255	Intermediate Similarity	NPD1799	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6939	Phase 2
0.6667	Remote Similarity	NPD4243	Approved
0.6522	Remote Similarity	NPD4747	Approved
0.6479	Remote Similarity	NPD4785	Approved
0.6479	Remote Similarity	NPD4784	Approved
0.6471	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7339	Approved
0.6389	Remote Similarity	NPD6942	Approved
0.6377	Remote Similarity	NPD4137	Phase 3
0.6286	Remote Similarity	NPD4691	Approved
0.625	Remote Similarity	NPD5733	Approved
0.6203	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7525	Registered
0.6164	Remote Similarity	NPD4190	Phase 3
0.6164	Remote Similarity	NPD5275	Approved
0.6143	Remote Similarity	NPD6923	Approved
0.6143	Remote Similarity	NPD6922	Approved
0.6056	Remote Similarity	NPD7143	Approved
0.6056	Remote Similarity	NPD7144	Approved
0.6027	Remote Similarity	NPD4058	Approved
0.6027	Remote Similarity	NPD4687	Approved
0.5972	Remote Similarity	NPD5276	Approved
0.5972	Remote Similarity	NPD7150	Approved
0.5972	Remote Similarity	NPD7152	Approved
0.5972	Remote Similarity	NPD7151	Approved
0.5949	Remote Similarity	NPD4788	Approved
0.5932	Remote Similarity	NPD8262	Approved
0.5867	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD7645	Phase 2
0.5844	Remote Similarity	NPD4195	Approved
0.5811	Remote Similarity	NPD6924	Approved
0.5811	Remote Similarity	NPD6926	Approved
0.5765	Remote Similarity	NPD8034	Phase 2
0.5765	Remote Similarity	NPD8035	Phase 2
0.5679	Remote Similarity	NPD4786	Approved
0.5658	Remote Similarity	NPD6933	Approved
0.5625	Remote Similarity	NPD4223	Phase 3
0.5625	Remote Similarity	NPD4221	Approved
0.561	Remote Similarity	NPD5329	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