NPASS Compound

Structure

CID173272 OpenBabel06191715542D 34 37 0 0 1 0 0 0 0 0999 V2000 4.7416 -4.1216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2808 -4.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3779 2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2526 2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3063 -3.2787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2803 -3.2785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8191 -2.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6894 1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6885 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2210 0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3770 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8440 -1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 -0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7676 -4.1218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -2.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6888 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5336 1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2212 1.4613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3583 -3.2793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5333 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9744 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 -5.0875 1.9609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3945 0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -4.1227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6157 -3.2796 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 27 1 0 0 0 0 4 27 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 20 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 19 10 1 1 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 6 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 31 1 6 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	5.429
LogD:	4.359
LogS:	-4.215
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	4.96
Fsp3:	0.833
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:	-5.296
MDCK Permeability:	1.2927302122989204e-05
Pgp-inhibitor:	0.331
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.391
Plasma Protein Binding (PPB):	94.64962005615234%
Volume Distribution (VD):	0.683
Pgp-substrate:	3.4178361892700195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.247
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	10.432
Half-life (T1/2):	0.191

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.713
Carcinogencity:	0.141
Eye Corrosion:	0.005
Eye Irritation:	0.052
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC173272

Natural Product ID:	NPC173272
*Common Name:**	15R-Hydroxytrametenolic Acid
IUPAC Name:	(2R)-2-[(3S,5R,10S,13R,14R,15S,17R)-3,15-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:	15R-Hydroxytrametenolic Acid
Standard InCHIKey:	QQFMRSAZKNSIDN-JZTHNVADSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(2)9-8-10-19(26(33)34)22-17-25(32)30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(22,30)6/h9,19,22-25,31-32H,8,10-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24+,25+,28-,29-,30-/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)O)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482587
PubChem CID:	44575773
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
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620242]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19842686]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13025	Senecio lanceus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11286	Helichrysum bilobum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9732	Glochidion heyneanum	Species	Phyllanthaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12000.0	nM	PMID[488946]

☑ 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 NPC173272 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	176
0.1-0.2	1150
0.2-0.3	4733
0.3-0.4	12545
0.4-0.5	9528
0.5-0.6	6004
0.6-0.7	5929
0.7-0.8	2270
0.8-0.85	250
0.85-0.9	90
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC48330
0.9444	High Similarity	NPC206810
0.9355	High Similarity	NPC477854
0.9348	High Similarity	NPC477853
0.9271	High Similarity	NPC477812
0.9213	High Similarity	NPC242864
0.913	High Similarity	NPC166906
0.9121	High Similarity	NPC23434
0.9101	High Similarity	NPC187376
0.9101	High Similarity	NPC159046
0.9101	High Similarity	NPC233836
0.9043	High Similarity	NPC190554
0.9032	High Similarity	NPC45324
0.9032	High Similarity	NPC470016
0.9032	High Similarity	NPC162001
0.9032	High Similarity	NPC222845
0.9032	High Similarity	NPC317586
0.9022	High Similarity	NPC470375
0.9022	High Similarity	NPC477855
0.9022	High Similarity	NPC470376
0.8989	High Similarity	NPC28252
0.8989	High Similarity	NPC55309
0.898	High Similarity	NPC231530
0.898	High Similarity	NPC278628
0.8947	High Similarity	NPC114274
0.8936	High Similarity	NPC95565
0.8936	High Similarity	NPC305483
0.8936	High Similarity	NPC96859
0.8936	High Similarity	NPC42042
0.8936	High Similarity	NPC328162
0.8913	High Similarity	NPC26888
0.8901	High Similarity	NPC102414
0.8901	High Similarity	NPC77168
0.8901	High Similarity	NPC84271
0.8901	High Similarity	NPC474704
0.8901	High Similarity	NPC475921
0.8889	High Similarity	NPC474684
0.8889	High Similarity	NPC142361
0.8866	High Similarity	NPC271980
0.8866	High Similarity	NPC193934
0.8854	High Similarity	NPC15390
0.8842	High Similarity	NPC108078
0.8842	High Similarity	NPC320306
0.883	High Similarity	NPC69548
0.883	High Similarity	NPC469599
0.883	High Similarity	NPC184848
0.8812	High Similarity	NPC197428
0.8804	High Similarity	NPC148414
0.8804	High Similarity	NPC111585
0.8804	High Similarity	NPC175628
0.8804	High Similarity	NPC469400
0.88	High Similarity	NPC94529
0.8778	High Similarity	NPC155011
0.8776	High Similarity	NPC55872
0.8776	High Similarity	NPC140723
0.875	High Similarity	NPC477813
0.875	High Similarity	NPC48647
0.875	High Similarity	NPC186810
0.875	High Similarity	NPC197386
0.8723	High Similarity	NPC469406
0.8723	High Similarity	NPC111015
0.871	High Similarity	NPC189520
0.871	High Similarity	NPC297265
0.87	High Similarity	NPC472925
0.8696	High Similarity	NPC54689
0.8696	High Similarity	NPC86319
0.8696	High Similarity	NPC275740
0.8696	High Similarity	NPC474889
0.8687	High Similarity	NPC28656
0.8687	High Similarity	NPC96268
0.8681	High Similarity	NPC312215
0.8673	High Similarity	NPC195290
0.8673	High Similarity	NPC204450
0.866	High Similarity	NPC83709
0.866	High Similarity	NPC218383
0.866	High Similarity	NPC316964
0.866	High Similarity	NPC327431
0.8646	High Similarity	NPC43747
0.8632	High Similarity	NPC173875
0.8632	High Similarity	NPC279974
0.8632	High Similarity	NPC174948
0.8632	High Similarity	NPC469995
0.8632	High Similarity	NPC127063
0.8632	High Similarity	NPC473240
0.8632	High Similarity	NPC318282
0.8617	High Similarity	NPC66429
0.8617	High Similarity	NPC152897
0.8617	High Similarity	NPC25750
0.8602	High Similarity	NPC20388
0.8602	High Similarity	NPC289213
0.8602	High Similarity	NPC471896
0.86	High Similarity	NPC323834
0.8587	High Similarity	NPC131470
0.8587	High Similarity	NPC294480
0.8587	High Similarity	NPC471722
0.8587	High Similarity	NPC143767
0.8586	High Similarity	NPC236390
0.8586	High Similarity	NPC191892
0.8586	High Similarity	NPC159442
0.8571	High Similarity	NPC94755
0.8571	High Similarity	NPC212843
0.8571	High Similarity	NPC472924
0.8542	High Similarity	NPC120708
0.8542	High Similarity	NPC328371
0.8542	High Similarity	NPC234564
0.8542	High Similarity	NPC476327
0.8542	High Similarity	NPC476318
0.8542	High Similarity	NPC49371
0.8526	High Similarity	NPC196485
0.8526	High Similarity	NPC245972
0.8515	High Similarity	NPC42847
0.8515	High Similarity	NPC64844
0.8511	High Similarity	NPC154101
0.8511	High Similarity	NPC110657
0.8511	High Similarity	NPC86266
0.8511	High Similarity	NPC212301
0.85	High Similarity	NPC471293
0.85	High Similarity	NPC29705
0.8495	Intermediate Similarity	NPC186688
0.8495	Intermediate Similarity	NPC128496
0.8485	Intermediate Similarity	NPC22388
0.8485	Intermediate Similarity	NPC293753
0.8485	Intermediate Similarity	NPC473424
0.8485	Intermediate Similarity	NPC234892
0.8485	Intermediate Similarity	NPC473788
0.8485	Intermediate Similarity	NPC475558
0.8469	Intermediate Similarity	NPC110149
0.8462	Intermediate Similarity	NPC280782
0.8462	Intermediate Similarity	NPC71348
0.8454	Intermediate Similarity	NPC18319
0.8454	Intermediate Similarity	NPC189880
0.8444	Intermediate Similarity	NPC278648
0.8444	Intermediate Similarity	NPC476082
0.8438	Intermediate Similarity	NPC263347
0.8438	Intermediate Similarity	NPC200702
0.8438	Intermediate Similarity	NPC472485
0.8438	Intermediate Similarity	NPC255809
0.8438	Intermediate Similarity	NPC472932
0.8438	Intermediate Similarity	NPC241156
0.8427	Intermediate Similarity	NPC473420
0.8421	Intermediate Similarity	NPC69454
0.8421	Intermediate Similarity	NPC470224
0.8421	Intermediate Similarity	NPC170220
0.8421	Intermediate Similarity	NPC244356
0.8421	Intermediate Similarity	NPC141497
0.8421	Intermediate Similarity	NPC107674
0.8421	Intermediate Similarity	NPC224060
0.8421	Intermediate Similarity	NPC243866
0.8416	Intermediate Similarity	NPC149047
0.8416	Intermediate Similarity	NPC196528
0.8404	Intermediate Similarity	NPC46281
0.8404	Intermediate Similarity	NPC183283
0.8404	Intermediate Similarity	NPC136801
0.84	Intermediate Similarity	NPC312900
0.84	Intermediate Similarity	NPC251017
0.8387	Intermediate Similarity	NPC53911
0.8387	Intermediate Similarity	NPC328539
0.8387	Intermediate Similarity	NPC328313
0.8387	Intermediate Similarity	NPC48866
0.8387	Intermediate Similarity	NPC193360
0.8387	Intermediate Similarity	NPC183546
0.8387	Intermediate Similarity	NPC247406
0.8384	Intermediate Similarity	NPC302537
0.8384	Intermediate Similarity	NPC163372
0.8381	Intermediate Similarity	NPC202889
0.837	Intermediate Similarity	NPC73038
0.837	Intermediate Similarity	NPC474970
0.837	Intermediate Similarity	NPC72133
0.8367	Intermediate Similarity	NPC58942
0.8367	Intermediate Similarity	NPC260149
0.8367	Intermediate Similarity	NPC10364
0.8367	Intermediate Similarity	NPC166745
0.8367	Intermediate Similarity	NPC119036
0.8367	Intermediate Similarity	NPC235464
0.8367	Intermediate Similarity	NPC471717
0.8365	Intermediate Similarity	NPC472928
0.8352	Intermediate Similarity	NPC59453
0.8352	Intermediate Similarity	NPC165064
0.8352	Intermediate Similarity	NPC124172
0.8352	Intermediate Similarity	NPC82902
0.8352	Intermediate Similarity	NPC221758
0.8351	Intermediate Similarity	NPC304899
0.8351	Intermediate Similarity	NPC125622
0.8351	Intermediate Similarity	NPC7124
0.8351	Intermediate Similarity	NPC155676
0.8351	Intermediate Similarity	NPC249954
0.8351	Intermediate Similarity	NPC253115
0.8333	Intermediate Similarity	NPC159365
0.8333	Intermediate Similarity	NPC475060
0.8333	Intermediate Similarity	NPC73882
0.8333	Intermediate Similarity	NPC474922
0.8333	Intermediate Similarity	NPC220229
0.8333	Intermediate Similarity	NPC59530
0.8333	Intermediate Similarity	NPC49670
0.8333	Intermediate Similarity	NPC470957
0.8333	Intermediate Similarity	NPC260956
0.8333	Intermediate Similarity	NPC165873
0.8333	Intermediate Similarity	NPC470958
0.8317	Intermediate Similarity	NPC204833
0.8317	Intermediate Similarity	NPC209502

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 NPC173272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1529
0.2-0.3	4007
0.3-0.4	2330
0.4-0.5	615
0.5-0.6	182
0.6-0.7	166
0.7-0.8	159
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD5328	Approved
0.8416	Intermediate Similarity	NPD5739	Approved
0.8416	Intermediate Similarity	NPD7128	Approved
0.8416	Intermediate Similarity	NPD6675	Approved
0.8416	Intermediate Similarity	NPD6402	Approved
0.8352	Intermediate Similarity	NPD4786	Approved
0.8316	Intermediate Similarity	NPD6079	Approved
0.8265	Intermediate Similarity	NPD4755	Approved
0.8252	Intermediate Similarity	NPD7320	Approved
0.8252	Intermediate Similarity	NPD6899	Approved
0.8252	Intermediate Similarity	NPD6881	Approved
0.8229	Intermediate Similarity	NPD6399	Phase 3
0.8173	Intermediate Similarity	NPD6372	Approved
0.8173	Intermediate Similarity	NPD6373	Approved
0.8155	Intermediate Similarity	NPD5701	Approved
0.8155	Intermediate Similarity	NPD5697	Approved
0.8132	Intermediate Similarity	NPD3667	Approved
0.81	Intermediate Similarity	NPD5286	Approved
0.81	Intermediate Similarity	NPD4696	Approved
0.81	Intermediate Similarity	NPD5285	Approved
0.81	Intermediate Similarity	NPD4700	Approved
0.8095	Intermediate Similarity	NPD6883	Approved
0.8095	Intermediate Similarity	NPD7290	Approved
0.8095	Intermediate Similarity	NPD7102	Approved
0.8077	Intermediate Similarity	NPD6011	Approved
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD6008	Approved
0.8041	Intermediate Similarity	NPD4202	Approved
0.8037	Intermediate Similarity	NPD4632	Approved
0.802	Intermediate Similarity	NPD5223	Approved
0.8019	Intermediate Similarity	NPD6847	Approved
0.8019	Intermediate Similarity	NPD6617	Approved
0.8019	Intermediate Similarity	NPD6650	Approved
0.8019	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD6869	Approved
0.8019	Intermediate Similarity	NPD6649	Approved
0.8019	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD4697	Phase 3
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3133	Approved
0.7944	Intermediate Similarity	NPD8297	Approved
0.7944	Intermediate Similarity	NPD6882	Approved
0.7941	Intermediate Similarity	NPD5226	Approved
0.7941	Intermediate Similarity	NPD4633	Approved
0.7941	Intermediate Similarity	NPD5211	Phase 2
0.7941	Intermediate Similarity	NPD5224	Approved
0.7941	Intermediate Similarity	NPD5225	Approved
0.7938	Intermediate Similarity	NPD7515	Phase 2
0.7921	Intermediate Similarity	NPD7640	Approved
0.7921	Intermediate Similarity	NPD7639	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7879	Intermediate Similarity	NPD5695	Phase 3
0.7864	Intermediate Similarity	NPD5175	Approved
0.7864	Intermediate Similarity	NPD4754	Approved
0.7864	Intermediate Similarity	NPD5174	Approved
0.7818	Intermediate Similarity	NPD6009	Approved
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD7146	Approved
0.7788	Intermediate Similarity	NPD5141	Approved
0.7757	Intermediate Similarity	NPD4634	Approved
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD6411	Approved
0.7755	Intermediate Similarity	NPD5281	Approved
0.7732	Intermediate Similarity	NPD4753	Phase 2
0.7714	Intermediate Similarity	NPD4767	Approved
0.7714	Intermediate Similarity	NPD4768	Approved
0.7692	Intermediate Similarity	NPD6115	Approved
0.7692	Intermediate Similarity	NPD6118	Approved
0.7692	Intermediate Similarity	NPD6114	Approved
0.7692	Intermediate Similarity	NPD6697	Approved
0.7667	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6903	Approved
0.7611	Intermediate Similarity	NPD6319	Approved
0.7604	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD7748	Approved
0.7589	Intermediate Similarity	NPD6335	Approved
0.7579	Intermediate Similarity	NPD3668	Phase 3
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.757	Intermediate Similarity	NPD5128	Approved
0.757	Intermediate Similarity	NPD4730	Approved
0.757	Intermediate Similarity	NPD4729	Approved
0.7568	Intermediate Similarity	NPD6274	Approved
0.7565	Intermediate Similarity	NPD7604	Phase 2
0.7556	Intermediate Similarity	NPD6942	Approved
0.7556	Intermediate Similarity	NPD7339	Approved
0.7553	Intermediate Similarity	NPD4223	Phase 3
0.7553	Intermediate Similarity	NPD4221	Approved
0.7551	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6101	Approved
0.7544	Intermediate Similarity	NPD5983	Phase 2
0.7527	Intermediate Similarity	NPD7525	Registered
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7101	Approved
0.7522	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7476	Intermediate Similarity	NPD5696	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7456	Intermediate Similarity	NPD6059	Approved
0.7456	Intermediate Similarity	NPD6054	Approved
0.7455	Intermediate Similarity	NPD6053	Discontinued
0.7449	Intermediate Similarity	NPD5737	Approved
0.7449	Intermediate Similarity	NPD6672	Approved
0.7436	Intermediate Similarity	NPD6336	Discontinued
0.7436	Intermediate Similarity	NPD6616	Approved
0.7434	Intermediate Similarity	NPD6314	Approved
0.7434	Intermediate Similarity	NPD6313	Approved
0.7431	Intermediate Similarity	NPD5135	Approved
0.7431	Intermediate Similarity	NPD5250	Approved
0.7431	Intermediate Similarity	NPD5169	Approved
0.7431	Intermediate Similarity	NPD5248	Approved
0.7431	Intermediate Similarity	NPD5251	Approved
0.7431	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5247	Approved
0.7431	Intermediate Similarity	NPD5249	Phase 3
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD6098	Approved
0.7423	Intermediate Similarity	NPD5280	Approved
0.7423	Intermediate Similarity	NPD4694	Approved
0.7411	Intermediate Similarity	NPD6868	Approved
0.74	Intermediate Similarity	NPD6050	Approved
0.7396	Intermediate Similarity	NPD4197	Approved
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7391	Intermediate Similarity	NPD6909	Approved
0.7391	Intermediate Similarity	NPD6908	Approved
0.7379	Intermediate Similarity	NPD7902	Approved
0.7374	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD6904	Approved
0.7374	Intermediate Similarity	NPD6080	Approved
0.7373	Intermediate Similarity	NPD7078	Approved
0.7373	Intermediate Similarity	NPD8293	Discontinued
0.7364	Intermediate Similarity	NPD5215	Approved
0.7364	Intermediate Similarity	NPD5127	Approved
0.7364	Intermediate Similarity	NPD5216	Approved
0.7364	Intermediate Similarity	NPD5217	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5210	Approved
0.7347	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5368	Approved
0.734	Intermediate Similarity	NPD4748	Discontinued
0.7328	Intermediate Similarity	NPD6370	Approved
0.7315	Intermediate Similarity	NPD6412	Phase 2
0.7311	Intermediate Similarity	NPD7736	Approved
0.73	Intermediate Similarity	NPD5692	Phase 3
0.7292	Intermediate Similarity	NPD4788	Approved
0.7292	Intermediate Similarity	NPD5362	Discontinued
0.7288	Intermediate Similarity	NPD7507	Approved
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.7263	Intermediate Similarity	NPD4139	Approved
0.7263	Intermediate Similarity	NPD4692	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5168	Approved
0.7245	Intermediate Similarity	NPD4138	Approved
0.7245	Intermediate Similarity	NPD4690	Approved
0.7245	Intermediate Similarity	NPD4693	Phase 3
0.7245	Intermediate Similarity	NPD5205	Approved
0.7245	Intermediate Similarity	NPD4689	Approved
0.7245	Intermediate Similarity	NPD4688	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7241	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5694	Approved
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD6435	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7174	Intermediate Similarity	NPD3703	Phase 2
0.7168	Intermediate Similarity	NPD5167	Approved
0.7129	Intermediate Similarity	NPD5207	Approved
0.7128	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7319	Approved
0.71	Intermediate Similarity	NPD5208	Approved
0.7087	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD6001	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5369	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7065	Intermediate Similarity	NPD4784	Approved
0.7065	Intermediate Similarity	NPD4785	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1

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