NPASS Compound

Structure

CID288035 OpenBabel06191716092D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.6329 5.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9993 6.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5418 5.6986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8089 3.7142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2057 4.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3514 3.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7482 3.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5721 5.5969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3817 2.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1753 4.7064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -0.9755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3815 1.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5358 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5361 1.4626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5557 -1.4752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 2 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 21 7 1 6 0 0 0 22 28 1 0 0 0 0 23 30 1 6 0 0 0 24 11 1 1 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 29 1 6 0 0 0 26 29 1 6 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.39
Volume:	482.068
LogP:	8.038
LogD:	6.816
LogS:	-6.905
# Rotatable Bonds:	6
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	4.388
Fsp3:	0.931
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:	-4.735
MDCK Permeability:	1.63798777066404e-05
Pgp-inhibitor:	0.922
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.74
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	92.7019271850586%
Volume Distribution (VD):	1.41
Pgp-substrate:	1.3792264461517334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.552
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.532
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.713

ADMET: Excretion

Clearance (CL):	6.021
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.791
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.468
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.244
Skin Sensitization:	0.96
Carcinogencity:	0.042
Eye Corrosion:	0.953
Eye Irritation:	0.854
Respiratory Toxicity:	0.313

Download Data

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

Natural Product: NPC288035

Natural Product ID:	NPC288035
*Common Name:**	(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-Ethyl-6-Methylheptan-2-Yl]-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-Dodecahydro-1H-Cyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	KZJWDPNRJALLNS-MHHBOJDBSA-N
Standard InCHI:	InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27-,28+,29-/m1/s1
SMILES:	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@@H]3CC[C@]12C)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3348885
PubChem CID:	7067829
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO10600	Dysoxylum spectabile	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO323	Trachelanthus hissaricus	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11864	Aflatunia ulmifolia	n.a.	n.a.	n.a.	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
Potency	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	7492.9	nM	PMID[493173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	3.3	nM	PMID[493173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	59.5	nM	PMID[493173]

☑ 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 NPC288035 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	154
0.1-0.2	1367
0.2-0.3	7998
0.3-0.4	15432
0.4-0.5	6900
0.5-0.6	5521
0.6-0.7	3864
0.7-0.8	1081
0.8-0.85	207
0.85-0.9	90
0.9-0.95	48
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304309
1.0	High Similarity	NPC134847
1.0	High Similarity	NPC162742
1.0	High Similarity	NPC22105
1.0	High Similarity	NPC136188
1.0	High Similarity	NPC285893
1.0	High Similarity	NPC230301
1.0	High Similarity	NPC28657
0.9857	High Similarity	NPC107059
0.9857	High Similarity	NPC240604
0.9857	High Similarity	NPC113733
0.9857	High Similarity	NPC300324
0.9857	High Similarity	NPC321381
0.9857	High Similarity	NPC321016
0.9718	High Similarity	NPC34019
0.9718	High Similarity	NPC198968
0.9718	High Similarity	NPC318495
0.9718	High Similarity	NPC155986
0.9714	High Similarity	NPC257347
0.9714	High Similarity	NPC471723
0.9714	High Similarity	NPC141071
0.9583	High Similarity	NPC477522
0.9583	High Similarity	NPC18603
0.9583	High Similarity	NPC307965
0.9583	High Similarity	NPC76931
0.9583	High Similarity	NPC473943
0.9583	High Similarity	NPC474216
0.9583	High Similarity	NPC87604
0.9577	High Similarity	NPC134330
0.9577	High Similarity	NPC189883
0.9577	High Similarity	NPC129165
0.9452	High Similarity	NPC328714
0.9452	High Similarity	NPC81306
0.9452	High Similarity	NPC84694
0.9452	High Similarity	NPC28862
0.9452	High Similarity	NPC109546
0.9452	High Similarity	NPC47982
0.9452	High Similarity	NPC143182
0.9324	High Similarity	NPC209944
0.9324	High Similarity	NPC26117
0.9324	High Similarity	NPC234193
0.9324	High Similarity	NPC241290
0.9324	High Similarity	NPC164840
0.9315	High Similarity	NPC275910
0.9306	High Similarity	NPC202642
0.9306	High Similarity	NPC96319
0.9306	High Similarity	NPC244488
0.9306	High Similarity	NPC470362
0.9306	High Similarity	NPC237460
0.9306	High Similarity	NPC46160
0.9306	High Similarity	NPC247325
0.92	High Similarity	NPC474731
0.92	High Similarity	NPC264245
0.92	High Similarity	NPC474759
0.92	High Similarity	NPC47761
0.92	High Similarity	NPC7505
0.92	High Similarity	NPC474531
0.92	High Similarity	NPC23852
0.92	High Similarity	NPC474683
0.92	High Similarity	NPC474752
0.92	High Similarity	NPC82986
0.92	High Similarity	NPC470383
0.92	High Similarity	NPC209620
0.9189	High Similarity	NPC1319
0.9189	High Similarity	NPC209430
0.9189	High Similarity	NPC30986
0.9178	High Similarity	NPC214570
0.9167	High Similarity	NPC322353
0.9167	High Similarity	NPC118508
0.9167	High Similarity	NPC121744
0.9155	High Similarity	NPC471799
0.9155	High Similarity	NPC474140
0.913	High Similarity	NPC160209
0.913	High Similarity	NPC208999
0.9079	High Similarity	NPC5985
0.9079	High Similarity	NPC50964
0.9079	High Similarity	NPC101462
0.9079	High Similarity	NPC189972
0.9079	High Similarity	NPC49964
0.9079	High Similarity	NPC470614
0.9079	High Similarity	NPC1272
0.9067	High Similarity	NPC236112
0.9054	High Similarity	NPC477514
0.9054	High Similarity	NPC138621
0.9054	High Similarity	NPC205455
0.9054	High Similarity	NPC6978
0.9054	High Similarity	NPC85346
0.9054	High Similarity	NPC167037
0.9054	High Similarity	NPC186191
0.9054	High Similarity	NPC285761
0.9054	High Similarity	NPC302041
0.9054	High Similarity	NPC65897
0.9054	High Similarity	NPC244385
0.9041	High Similarity	NPC73875
0.9028	High Similarity	NPC469533
0.9028	High Similarity	NPC471797
0.9028	High Similarity	NPC469534
0.9028	High Similarity	NPC469593
0.8961	High Similarity	NPC317458
0.8961	High Similarity	NPC474634
0.8961	High Similarity	NPC475789
0.8933	High Similarity	NPC273410
0.8933	High Similarity	NPC80530
0.8904	High Similarity	NPC471468
0.8889	High Similarity	NPC182717
0.8889	High Similarity	NPC201373
0.8873	High Similarity	NPC145498
0.8873	High Similarity	NPC475728
0.8846	High Similarity	NPC185568
0.8846	High Similarity	NPC205845
0.8846	High Similarity	NPC209802
0.8846	High Similarity	NPC124172
0.8846	High Similarity	NPC33913
0.8846	High Similarity	NPC472265
0.8846	High Similarity	NPC59453
0.8846	High Similarity	NPC221758
0.8831	High Similarity	NPC248886
0.8831	High Similarity	NPC201852
0.8831	High Similarity	NPC470049
0.8831	High Similarity	NPC30166
0.8816	High Similarity	NPC322313
0.8816	High Similarity	NPC102253
0.8816	High Similarity	NPC236237
0.8816	High Similarity	NPC13554
0.88	High Similarity	NPC312328
0.88	High Similarity	NPC318136
0.8784	High Similarity	NPC106364
0.8767	High Similarity	NPC243342
0.8767	High Similarity	NPC477138
0.8767	High Similarity	NPC329090
0.8767	High Similarity	NPC27395
0.8767	High Similarity	NPC100334
0.875	High Similarity	NPC111234
0.875	High Similarity	NPC242001
0.8734	High Similarity	NPC274448
0.8734	High Similarity	NPC157257
0.8734	High Similarity	NPC474189
0.8734	High Similarity	NPC266511
0.8734	High Similarity	NPC474349
0.8732	High Similarity	NPC269877
0.8732	High Similarity	NPC167272
0.8714	High Similarity	NPC197805
0.8684	High Similarity	NPC472463
0.8667	High Similarity	NPC471798
0.8649	High Similarity	NPC66566
0.8649	High Similarity	NPC477923
0.8649	High Similarity	NPC328104
0.8649	High Similarity	NPC291503
0.8649	High Similarity	NPC319090
0.863	High Similarity	NPC195489
0.8625	High Similarity	NPC31564
0.8625	High Similarity	NPC6391
0.8625	High Similarity	NPC474778
0.8625	High Similarity	NPC145879
0.8625	High Similarity	NPC261266
0.8625	High Similarity	NPC474732
0.8625	High Similarity	NPC477604
0.8625	High Similarity	NPC293287
0.8625	High Similarity	NPC155011
0.8625	High Similarity	NPC24277
0.8625	High Similarity	NPC474970
0.8625	High Similarity	NPC51014
0.8625	High Similarity	NPC94462
0.8625	High Similarity	NPC152808
0.8625	High Similarity	NPC474733
0.8611	High Similarity	NPC45296
0.8611	High Similarity	NPC9161
0.8611	High Similarity	NPC49422
0.8608	High Similarity	NPC470077
0.8608	High Similarity	NPC478102
0.8608	High Similarity	NPC238485
0.8608	High Similarity	NPC474047
0.859	High Similarity	NPC20853
0.859	High Similarity	NPC87489
0.859	High Similarity	NPC296701
0.859	High Similarity	NPC151519
0.859	High Similarity	NPC218616
0.859	High Similarity	NPC202389
0.8571	High Similarity	NPC222366
0.8571	High Similarity	NPC286669
0.8571	High Similarity	NPC476039
0.8553	High Similarity	NPC167891
0.8553	High Similarity	NPC474989
0.8553	High Similarity	NPC83351
0.8553	High Similarity	NPC22955
0.8553	High Similarity	NPC470396
0.8553	High Similarity	NPC99168
0.8553	High Similarity	NPC475337
0.8551	High Similarity	NPC290367
0.8533	High Similarity	NPC120098
0.8533	High Similarity	NPC265328
0.8533	High Similarity	NPC315261
0.8533	High Similarity	NPC290598
0.8533	High Similarity	NPC274079
0.8533	High Similarity	NPC477925
0.8533	High Similarity	NPC122418
0.8533	High Similarity	NPC27765
0.8533	High Similarity	NPC30590
0.8519	High Similarity	NPC58063
0.8519	High Similarity	NPC475313

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 NPC288035 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1632
0.2-0.3	4499
0.3-0.4	1999
0.4-0.5	431
0.5-0.6	175
0.6-0.7	145
0.7-0.8	74
0.8-0.85	15
0.85-0.9	16
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7339	Approved
1.0	High Similarity	NPD6942	Approved
0.9306	High Similarity	NPD3701	Clinical (unspecified phase)
0.8846	High Similarity	NPD4786	Approved
0.8816	High Similarity	NPD7525	Registered
0.8767	High Similarity	NPD4784	Approved
0.8767	High Similarity	NPD6926	Approved
0.8767	High Similarity	NPD4785	Approved
0.8767	High Similarity	NPD6924	Approved
0.875	High Similarity	NPD4243	Approved
0.875	High Similarity	NPD7152	Approved
0.875	High Similarity	NPD7150	Approved
0.875	High Similarity	NPD7151	Approved
0.8732	High Similarity	NPD6922	Approved
0.8732	High Similarity	NPD6923	Approved
0.8611	High Similarity	NPD7143	Approved
0.8611	High Similarity	NPD7144	Approved
0.859	High Similarity	NPD3667	Approved
0.8533	High Similarity	NPD6933	Approved
0.8293	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6929	Approved
0.8205	Intermediate Similarity	NPD7645	Phase 2
0.8158	Intermediate Similarity	NPD5275	Approved
0.8158	Intermediate Similarity	NPD4190	Phase 3
0.8101	Intermediate Similarity	NPD6930	Phase 2
0.8101	Intermediate Similarity	NPD4748	Discontinued
0.8101	Intermediate Similarity	NPD6931	Approved
0.8095	Intermediate Similarity	NPD5328	Approved
0.7952	Intermediate Similarity	NPD3618	Phase 1
0.7949	Intermediate Similarity	NPD6925	Approved
0.7949	Intermediate Similarity	NPD5776	Phase 2
0.7949	Intermediate Similarity	NPD6932	Approved
0.7927	Intermediate Similarity	NPD3665	Phase 1
0.7927	Intermediate Similarity	NPD3666	Approved
0.7927	Intermediate Similarity	NPD3133	Approved
0.7907	Intermediate Similarity	NPD6079	Approved
0.7875	Intermediate Similarity	NPD7509	Discontinued
0.7848	Intermediate Similarity	NPD7145	Approved
0.7816	Intermediate Similarity	NPD6399	Phase 3
0.7805	Intermediate Similarity	NPD6695	Phase 3
0.775	Intermediate Similarity	NPD6683	Phase 2
0.775	Intermediate Similarity	NPD4195	Approved
0.7711	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3668	Phase 3
0.7654	Intermediate Similarity	NPD7514	Phase 3
0.7625	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6893	Approved
0.7614	Intermediate Similarity	NPD4202	Approved
0.7561	Intermediate Similarity	NPD6902	Approved
0.7529	Intermediate Similarity	NPD5279	Phase 3
0.7471	Intermediate Similarity	NPD4753	Phase 2
0.747	Intermediate Similarity	NPD4221	Approved
0.747	Intermediate Similarity	NPD4223	Phase 3
0.7468	Intermediate Similarity	NPD8264	Approved
0.7442	Intermediate Similarity	NPD7750	Discontinued
0.7442	Intermediate Similarity	NPD7524	Approved
0.7439	Intermediate Similarity	NPD7332	Phase 2
0.7412	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5329	Approved
0.7363	Intermediate Similarity	NPD4697	Phase 3
0.7363	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5221	Approved
0.7363	Intermediate Similarity	NPD5222	Approved
0.7349	Intermediate Similarity	NPD6898	Phase 1
0.7294	Intermediate Similarity	NPD4197	Approved
0.7283	Intermediate Similarity	NPD5173	Approved
0.7283	Intermediate Similarity	NPD4755	Approved
0.7176	Intermediate Similarity	NPD4788	Approved
0.7128	Intermediate Similarity	NPD5286	Approved
0.7128	Intermediate Similarity	NPD4700	Approved
0.7128	Intermediate Similarity	NPD4696	Approved
0.7128	Intermediate Similarity	NPD5285	Approved
0.7126	Intermediate Similarity	NPD4138	Approved
0.7126	Intermediate Similarity	NPD4693	Phase 3
0.7126	Intermediate Similarity	NPD5205	Approved
0.7126	Intermediate Similarity	NPD4689	Approved
0.7126	Intermediate Similarity	NPD4690	Approved
0.7126	Intermediate Similarity	NPD4688	Approved
0.7126	Intermediate Similarity	NPD7521	Approved
0.7126	Intermediate Similarity	NPD7334	Approved
0.7126	Intermediate Similarity	NPD6684	Approved
0.7126	Intermediate Similarity	NPD7146	Approved
0.7126	Intermediate Similarity	NPD6409	Approved
0.7126	Intermediate Similarity	NPD5330	Approved
0.7111	Intermediate Similarity	NPD7087	Discontinued
0.7111	Intermediate Similarity	NPD7515	Phase 2
0.7097	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD6083	Phase 2
0.7079	Intermediate Similarity	NPD6051	Approved
0.7065	Intermediate Similarity	NPD5210	Approved
0.7065	Intermediate Similarity	NPD4629	Approved
0.7053	Intermediate Similarity	NPD5223	Approved
0.7051	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7638	Approved
0.7021	Intermediate Similarity	NPD5290	Discontinued
0.6988	Remote Similarity	NPD3617	Approved
0.6979	Remote Similarity	NPD4633	Approved
0.6979	Remote Similarity	NPD5224	Approved
0.6979	Remote Similarity	NPD5225	Approved
0.6979	Remote Similarity	NPD5226	Approved
0.6979	Remote Similarity	NPD5211	Phase 2
0.6966	Remote Similarity	NPD4723	Approved
0.6966	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6672	Approved
0.6966	Remote Similarity	NPD4722	Approved
0.6966	Remote Similarity	NPD5737	Approved
0.6966	Remote Similarity	NPD6903	Approved
0.6962	Remote Similarity	NPD4787	Phase 1
0.6947	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD7639	Approved
0.6939	Remote Similarity	NPD5739	Approved
0.6939	Remote Similarity	NPD6675	Approved
0.6939	Remote Similarity	NPD6402	Approved
0.6939	Remote Similarity	NPD7128	Approved
0.6932	Remote Similarity	NPD4694	Approved
0.6932	Remote Similarity	NPD5280	Approved
0.6932	Remote Similarity	NPD5690	Phase 2
0.6907	Remote Similarity	NPD5174	Approved
0.6907	Remote Similarity	NPD4754	Approved
0.6907	Remote Similarity	NPD5175	Approved
0.6875	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5141	Approved
0.6824	Remote Similarity	NPD4695	Discontinued
0.68	Remote Similarity	NPD7320	Approved
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD7748	Approved
0.6768	Remote Similarity	NPD4767	Approved
0.6768	Remote Similarity	NPD4768	Approved
0.675	Remote Similarity	NPD4747	Approved
0.6744	Remote Similarity	NPD4139	Approved
0.6744	Remote Similarity	NPD4692	Approved
0.6742	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6098	Approved
0.6739	Remote Similarity	NPD8034	Phase 2
0.6739	Remote Similarity	NPD8035	Phase 2
0.6739	Remote Similarity	NPD7637	Suspended
0.6733	Remote Similarity	NPD6372	Approved
0.6733	Remote Similarity	NPD6373	Approved
0.6709	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5695	Phase 3
0.67	Remote Similarity	NPD5697	Approved
0.67	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6634	Remote Similarity	NPD5128	Approved
0.6634	Remote Similarity	NPD6011	Approved
0.6634	Remote Similarity	NPD5168	Approved
0.6634	Remote Similarity	NPD4729	Approved
0.6634	Remote Similarity	NPD4730	Approved
0.663	Remote Similarity	NPD7136	Phase 2
0.6625	Remote Similarity	NPD4137	Phase 3
0.6625	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6847	Approved
0.6602	Remote Similarity	NPD8130	Phase 1
0.6602	Remote Similarity	NPD6650	Approved
0.6602	Remote Similarity	NPD6617	Approved
0.6602	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6649	Approved
0.6602	Remote Similarity	NPD6869	Approved
0.6579	Remote Similarity	NPD368	Approved
0.6569	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD6014	Approved
0.6569	Remote Similarity	NPD6013	Approved
0.6562	Remote Similarity	NPD7902	Approved
0.6559	Remote Similarity	NPD5281	Approved
0.6559	Remote Similarity	NPD5284	Approved
0.6556	Remote Similarity	NPD4519	Discontinued
0.6556	Remote Similarity	NPD4623	Approved
0.6548	Remote Similarity	NPD6117	Approved
0.6543	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4245	Approved
0.6543	Remote Similarity	NPD6939	Phase 2
0.6543	Remote Similarity	NPD4244	Approved
0.6543	Remote Similarity	NPD4789	Approved
0.6543	Remote Similarity	NPD4691	Approved
0.6538	Remote Similarity	NPD6882	Approved
0.6538	Remote Similarity	NPD8297	Approved
0.6538	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6412	Phase 2
0.6531	Remote Similarity	NPD4159	Approved
0.6522	Remote Similarity	NPD6673	Approved
0.6522	Remote Similarity	NPD6904	Approved
0.6522	Remote Similarity	NPD6080	Approved
0.6506	Remote Similarity	NPD5733	Approved
0.6505	Remote Similarity	NPD5249	Phase 3
0.6505	Remote Similarity	NPD5169	Approved
0.6505	Remote Similarity	NPD5248	Approved
0.6505	Remote Similarity	NPD5250	Approved
0.6505	Remote Similarity	NPD5251	Approved
0.6505	Remote Similarity	NPD5247	Approved
0.6505	Remote Similarity	NPD5135	Approved
0.6505	Remote Similarity	NPD4634	Approved
0.6505	Remote Similarity	NPD5134	Clinical (unspecified phase)

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