NPASS Compound

Structure

CID234193 OpenBabel06191716032D 31 34 0 0 1 0 0 0 0 0999 V2000 -4.1294 5.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1284 2.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5911 2.9246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2041 3.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6902 1.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6166 4.6136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6662 2.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1540 3.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3797 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6161 2.9249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6913 2.9258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1289 3.7694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6907 -0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3800 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8451 0.4882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 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 1.6905 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2462 -1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8656 -1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 20 7 1 6 0 0 0 21 28 1 0 0 0 0 22 30 1 6 0 0 0 23 29 1 6 0 0 0 24 27 1 0 0 0 0 24 29 1 6 0 0 0 25 27 1 0 0 0 0 25 28 1 6 0 0 0 26 27 1 0 0 0 0 26 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.37
Volume:	488.222
LogP:	6.106
LogD:	5.468
LogS:	-5.805
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	4.796
Fsp3:	0.862
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:	-4.608
MDCK Permeability:	2.0946579752489924e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.676

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	88.40975189208984%
Volume Distribution (VD):	1.039
Pgp-substrate:	1.0349043607711792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.157
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.324
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.373
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	2.847
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.695
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.241
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC234193

Natural Product ID:	NPC234193
*Common Name:**	7Beta-Hydroxystigmasterol
IUPAC Name:	(3S,7R,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Synonyms:	7Beta-Hydroxystigmasterol
Standard InCHIKey:	DPNNWDOFSGOYEK-IWIJBSIZSA-N
Standard InCHI:	InChI=1S/C29H48O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h8-9,17-20,22-27,30-31H,7,10-16H2,1-6H3/b9-8+/t19-,20-,22+,23-,24+,25+,26+,27+,28+,29-/m1/s1
SMILES:	CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H](O)C=C2[C@]1(C)CC[C@@H](C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455107
PubChem CID:	6442694
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
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO14556	Iris missouriensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655793]
NPO14556	Iris missouriensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734815]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14556	Iris missouriensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.1	ug ml-1	PMID[494332]

☑ 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 NPC234193 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	148
0.1-0.2	1221
0.2-0.3	5303
0.3-0.4	15542
0.4-0.5	8560
0.5-0.6	6078
0.6-0.7	4191
0.7-0.8	1256
0.8-0.85	226
0.85-0.9	87
0.9-0.95	64
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC264245
0.9865	High Similarity	NPC109546
0.9865	High Similarity	NPC84694
0.9865	High Similarity	NPC47982
0.9865	High Similarity	NPC28862
0.9865	High Similarity	NPC143182
0.9865	High Similarity	NPC81306
0.9737	High Similarity	NPC50964
0.9737	High Similarity	NPC49964
0.9733	High Similarity	NPC241290
0.9733	High Similarity	NPC164840
0.9733	High Similarity	NPC209944
0.973	High Similarity	NPC474216
0.9605	High Similarity	NPC209620
0.9605	High Similarity	NPC47761
0.9605	High Similarity	NPC23852
0.96	High Similarity	NPC209430
0.96	High Similarity	NPC30986
0.9487	High Similarity	NPC205845
0.9481	High Similarity	NPC101462
0.9481	High Similarity	NPC189972
0.9467	High Similarity	NPC473943
0.9459	High Similarity	NPC321381
0.9459	High Similarity	NPC107059
0.9459	High Similarity	NPC247325
0.9459	High Similarity	NPC244488
0.9459	High Similarity	NPC321016
0.9459	High Similarity	NPC113733
0.9367	High Similarity	NPC274448
0.9359	High Similarity	NPC475789
0.9359	High Similarity	NPC474634
0.9359	High Similarity	NPC317458
0.9351	High Similarity	NPC7505
0.9351	High Similarity	NPC82986
0.9351	High Similarity	NPC474731
0.9351	High Similarity	NPC474683
0.9351	High Similarity	NPC474752
0.9351	High Similarity	NPC474759
0.9333	High Similarity	NPC318495
0.9333	High Similarity	NPC198968
0.9333	High Similarity	NPC155986
0.9324	High Similarity	NPC28657
0.9324	High Similarity	NPC285893
0.9324	High Similarity	NPC22105
0.9324	High Similarity	NPC162742
0.9324	High Similarity	NPC134847
0.9324	High Similarity	NPC136188
0.9324	High Similarity	NPC304309
0.9324	High Similarity	NPC288035
0.9324	High Similarity	NPC230301
0.925	High Similarity	NPC261266
0.9241	High Similarity	NPC185568
0.9241	High Similarity	NPC238485
0.9231	High Similarity	NPC87489
0.9231	High Similarity	NPC296701
0.9231	High Similarity	NPC218616
0.9211	High Similarity	NPC167891
0.9211	High Similarity	NPC83351
0.9211	High Similarity	NPC76931
0.9211	High Similarity	NPC18603
0.9211	High Similarity	NPC477522
0.9211	High Similarity	NPC307965
0.9211	High Similarity	NPC87604
0.92	High Similarity	NPC240604
0.92	High Similarity	NPC129165
0.92	High Similarity	NPC300324
0.92	High Similarity	NPC134330
0.9136	High Similarity	NPC149224
0.9125	High Similarity	NPC266511
0.9125	High Similarity	NPC157257
0.9114	High Similarity	NPC470384
0.9091	High Similarity	NPC328714
0.9079	High Similarity	NPC91594
0.9079	High Similarity	NPC34019
0.9067	High Similarity	NPC471723
0.9067	High Similarity	NPC141071
0.9067	High Similarity	NPC257347
0.9054	High Similarity	NPC471799
0.9012	High Similarity	NPC6391
0.9012	High Similarity	NPC293287
0.9012	High Similarity	NPC152808
0.9	High Similarity	NPC231310
0.9	High Similarity	NPC470077
0.9	High Similarity	NPC474047
0.8987	High Similarity	NPC470049
0.8987	High Similarity	NPC202389
0.8974	High Similarity	NPC26117
0.8961	High Similarity	NPC477514
0.8961	High Similarity	NPC275910
0.8947	High Similarity	NPC96319
0.8947	High Similarity	NPC189883
0.8947	High Similarity	NPC470362
0.8933	High Similarity	NPC469533
0.8933	High Similarity	NPC469534
0.8933	High Similarity	NPC469593
0.8933	High Similarity	NPC471797
0.8889	High Similarity	NPC470360
0.8889	High Similarity	NPC318390
0.8875	High Similarity	NPC82623
0.8861	High Similarity	NPC470383
0.8861	High Similarity	NPC474531
0.8861	High Similarity	NPC476646
0.8846	High Similarity	NPC1319
0.8831	High Similarity	NPC214570
0.881	High Similarity	NPC204188
0.881	High Similarity	NPC80561
0.881	High Similarity	NPC295668
0.881	High Similarity	NPC329596
0.881	High Similarity	NPC3345
0.881	High Similarity	NPC291484
0.881	High Similarity	NPC11216
0.88	High Similarity	NPC474140
0.8795	High Similarity	NPC133588
0.8795	High Similarity	NPC474668
0.8784	High Similarity	NPC34834
0.878	High Similarity	NPC299068
0.8765	High Similarity	NPC33913
0.875	High Similarity	NPC470614
0.875	High Similarity	NPC1272
0.875	High Similarity	NPC5985
0.8734	High Similarity	NPC96362
0.8734	High Similarity	NPC236112
0.8718	High Similarity	NPC167037
0.8718	High Similarity	NPC285761
0.8718	High Similarity	NPC11908
0.8718	High Similarity	NPC244385
0.8718	High Similarity	NPC476314
0.8718	High Similarity	NPC6978
0.8718	High Similarity	NPC138621
0.8706	High Similarity	NPC41554
0.8706	High Similarity	NPC97404
0.8701	High Similarity	NPC237460
0.8701	High Similarity	NPC202642
0.8701	High Similarity	NPC265588
0.8701	High Similarity	NPC253190
0.8701	High Similarity	NPC73875
0.8701	High Similarity	NPC46160
0.869	High Similarity	NPC470361
0.869	High Similarity	NPC477606
0.869	High Similarity	NPC146554
0.8684	High Similarity	NPC243342
0.8684	High Similarity	NPC477138
0.8667	High Similarity	NPC242001
0.8659	High Similarity	NPC471224
0.8642	High Similarity	NPC134481
0.8642	High Similarity	NPC470558
0.8608	High Similarity	NPC80530
0.8608	High Similarity	NPC273410
0.859	High Similarity	NPC471798
0.859	High Similarity	NPC470758
0.859	High Similarity	NPC470711
0.8588	High Similarity	NPC48010
0.8571	High Similarity	NPC118508
0.8571	High Similarity	NPC291503
0.8571	High Similarity	NPC121744
0.8571	High Similarity	NPC471468
0.8571	High Similarity	NPC67872
0.8571	High Similarity	NPC322353
0.8571	High Similarity	NPC185536
0.8571	High Similarity	NPC471952
0.8554	High Similarity	NPC139724
0.8553	High Similarity	NPC182717
0.8553	High Similarity	NPC474743
0.8537	High Similarity	NPC221758
0.8537	High Similarity	NPC472265
0.8537	High Similarity	NPC124172
0.8537	High Similarity	NPC209802
0.8537	High Similarity	NPC59453
0.8533	High Similarity	NPC475728
0.8533	High Similarity	NPC145498
0.8519	High Similarity	NPC30166
0.8519	High Similarity	NPC248886
0.8519	High Similarity	NPC201852
0.8514	High Similarity	NPC160209
0.8514	High Similarity	NPC208999
0.8506	High Similarity	NPC292793
0.85	High Similarity	NPC102253
0.85	High Similarity	NPC322313
0.85	High Similarity	NPC236237
0.85	High Similarity	NPC295131
0.85	High Similarity	NPC13554
0.8488	Intermediate Similarity	NPC475806
0.8481	Intermediate Similarity	NPC186191
0.8481	Intermediate Similarity	NPC205455
0.8481	Intermediate Similarity	NPC65897
0.8481	Intermediate Similarity	NPC302041
0.8481	Intermediate Similarity	NPC85346
0.8471	Intermediate Similarity	NPC309603
0.8471	Intermediate Similarity	NPC2983
0.8471	Intermediate Similarity	NPC473999
0.8471	Intermediate Similarity	NPC262858
0.8471	Intermediate Similarity	NPC472240
0.8462	Intermediate Similarity	NPC470749
0.8452	Intermediate Similarity	NPC470620
0.8452	Intermediate Similarity	NPC58063
0.8442	Intermediate Similarity	NPC329090
0.8442	Intermediate Similarity	NPC201048
0.8442	Intermediate Similarity	NPC306727
0.8442	Intermediate Similarity	NPC27395
0.8442	Intermediate Similarity	NPC476366

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 NPC234193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1383
0.2-0.3	4158
0.3-0.4	2393
0.4-0.5	608
0.5-0.6	189
0.6-0.7	176
0.7-0.8	68
0.8-0.85	24
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9324	High Similarity	NPD7339	Approved
0.9324	High Similarity	NPD6942	Approved
0.8947	High Similarity	NPD3701	Clinical (unspecified phase)
0.8675	High Similarity	NPD4751	Clinical (unspecified phase)
0.8537	High Similarity	NPD4786	Approved
0.85	High Similarity	NPD7525	Registered
0.8442	Intermediate Similarity	NPD4785	Approved
0.8442	Intermediate Similarity	NPD4784	Approved
0.8442	Intermediate Similarity	NPD6926	Approved
0.8442	Intermediate Similarity	NPD6924	Approved
0.8421	Intermediate Similarity	NPD7152	Approved
0.8421	Intermediate Similarity	NPD7150	Approved
0.8421	Intermediate Similarity	NPD7151	Approved
0.8375	Intermediate Similarity	NPD6929	Approved
0.8293	Intermediate Similarity	NPD3667	Approved
0.8289	Intermediate Similarity	NPD7143	Approved
0.8289	Intermediate Similarity	NPD7144	Approved
0.8272	Intermediate Similarity	NPD7514	Phase 3
0.8272	Intermediate Similarity	NPD6930	Phase 2
0.8272	Intermediate Similarity	NPD6931	Approved
0.825	Intermediate Similarity	NPD7145	Approved
0.825	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6933	Approved
0.8182	Intermediate Similarity	NPD4243	Approved
0.8171	Intermediate Similarity	NPD6902	Approved
0.8158	Intermediate Similarity	NPD6923	Approved
0.8158	Intermediate Similarity	NPD6922	Approved
0.8125	Intermediate Similarity	NPD6925	Approved
0.8125	Intermediate Similarity	NPD5776	Phase 2
0.8101	Intermediate Similarity	NPD8264	Approved
0.8049	Intermediate Similarity	NPD7332	Phase 2
0.7976	Intermediate Similarity	NPD6695	Phase 3
0.7927	Intermediate Similarity	NPD7645	Phase 2
0.7901	Intermediate Similarity	NPD6932	Approved
0.7882	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6079	Approved
0.7841	Intermediate Similarity	NPD5328	Approved
0.7831	Intermediate Similarity	NPD4748	Discontinued
0.7791	Intermediate Similarity	NPD6893	Approved
0.7711	Intermediate Similarity	NPD4195	Approved
0.7701	Intermediate Similarity	NPD3618	Phase 1
0.7674	Intermediate Similarity	NPD3665	Phase 1
0.7674	Intermediate Similarity	NPD3666	Approved
0.7674	Intermediate Similarity	NPD3133	Approved
0.7654	Intermediate Similarity	NPD5275	Approved
0.7654	Intermediate Similarity	NPD4190	Phase 3
0.7619	Intermediate Similarity	NPD7509	Discontinued
0.7614	Intermediate Similarity	NPD7524	Approved
0.7614	Intermediate Similarity	NPD7750	Discontinued
0.7582	Intermediate Similarity	NPD6399	Phase 3
0.7529	Intermediate Similarity	NPD6898	Phase 1
0.75	Intermediate Similarity	NPD6683	Phase 2
0.7471	Intermediate Similarity	NPD3668	Phase 3
0.7391	Intermediate Similarity	NPD4202	Approved
0.734	Intermediate Similarity	NPD5221	Approved
0.734	Intermediate Similarity	NPD5222	Approved
0.734	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5211	Phase 2
0.7303	Intermediate Similarity	NPD5279	Phase 3
0.7292	Intermediate Similarity	NPD7639	Approved
0.7292	Intermediate Similarity	NPD7640	Approved
0.7283	Intermediate Similarity	NPD7637	Suspended
0.7283	Intermediate Similarity	NPD7087	Discontinued
0.7263	Intermediate Similarity	NPD5173	Approved
0.7253	Intermediate Similarity	NPD6051	Approved
0.7253	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD4221	Approved
0.7241	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5329	Approved
0.7188	Intermediate Similarity	NPD7638	Approved
0.7172	Intermediate Similarity	NPD5141	Approved
0.7158	Intermediate Similarity	NPD4697	Phase 3
0.7113	Intermediate Similarity	NPD5285	Approved
0.7113	Intermediate Similarity	NPD5286	Approved
0.7113	Intermediate Similarity	NPD4696	Approved
0.7111	Intermediate Similarity	NPD4623	Approved
0.7111	Intermediate Similarity	NPD4519	Discontinued
0.7083	Intermediate Similarity	NPD4755	Approved
0.7079	Intermediate Similarity	NPD4197	Approved
0.7053	Intermediate Similarity	NPD4629	Approved
0.7053	Intermediate Similarity	NPD5210	Approved
0.7041	Intermediate Similarity	NPD5223	Approved
0.7013	Intermediate Similarity	NPD368	Approved
0.701	Intermediate Similarity	NPD5290	Discontinued
0.6989	Remote Similarity	NPD7136	Phase 2
0.6977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5226	Approved
0.697	Remote Similarity	NPD5225	Approved
0.697	Remote Similarity	NPD4633	Approved
0.697	Remote Similarity	NPD5224	Approved
0.6966	Remote Similarity	NPD4788	Approved
0.6939	Remote Similarity	NPD4700	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD7334	Approved
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD5205	Approved
0.6916	Remote Similarity	NPD7115	Discovery
0.6915	Remote Similarity	NPD7515	Phase 2
0.6907	Remote Similarity	NPD6084	Phase 2
0.6907	Remote Similarity	NPD6083	Phase 2
0.69	Remote Similarity	NPD5175	Approved
0.69	Remote Similarity	NPD5174	Approved
0.6892	Remote Similarity	NPD342	Phase 1
0.6829	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6899	Approved
0.6796	Remote Similarity	NPD6881	Approved
0.6782	Remote Similarity	NPD3617	Approved
0.6778	Remote Similarity	NPD5362	Discontinued
0.6778	Remote Similarity	NPD5332	Approved
0.6778	Remote Similarity	NPD5331	Approved
0.6774	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6903	Approved
0.6774	Remote Similarity	NPD4722	Approved
0.6774	Remote Similarity	NPD6672	Approved
0.6774	Remote Similarity	NPD5737	Approved
0.6774	Remote Similarity	NPD4723	Approved
0.6765	Remote Similarity	NPD5739	Approved
0.6765	Remote Similarity	NPD7128	Approved
0.6765	Remote Similarity	NPD6402	Approved
0.6765	Remote Similarity	NPD6675	Approved
0.6747	Remote Similarity	NPD4787	Phase 1
0.6742	Remote Similarity	NPD4790	Discontinued
0.6739	Remote Similarity	NPD4694	Approved
0.6739	Remote Similarity	NPD5280	Approved
0.6733	Remote Similarity	NPD4754	Approved
0.67	Remote Similarity	NPD4159	Approved
0.6699	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7320	Approved
0.6635	Remote Similarity	NPD5168	Approved
0.6635	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD4729	Approved
0.6635	Remote Similarity	NPD4730	Approved
0.6634	Remote Similarity	NPD7632	Discontinued
0.6629	Remote Similarity	NPD4820	Approved
0.6629	Remote Similarity	NPD4822	Approved
0.6629	Remote Similarity	NPD4819	Approved
0.6629	Remote Similarity	NPD4821	Approved
0.6629	Remote Similarity	NPD4695	Discontinued
0.6604	Remote Similarity	NPD6847	Approved
0.6604	Remote Similarity	NPD8130	Phase 1
0.6604	Remote Similarity	NPD6650	Approved
0.6604	Remote Similarity	NPD6617	Approved
0.6604	Remote Similarity	NPD6869	Approved
0.6604	Remote Similarity	NPD6649	Approved
0.6602	Remote Similarity	NPD4768	Approved
0.6602	Remote Similarity	NPD4767	Approved
0.6598	Remote Similarity	NPD7748	Approved
0.6598	Remote Similarity	NPD5771	Approved
0.6591	Remote Similarity	NPD4271	Approved
0.6591	Remote Similarity	NPD4268	Approved
0.6579	Remote Similarity	NPD4219	Approved
0.6571	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6014	Approved
0.6571	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD6372	Approved
0.6571	Remote Similarity	NPD6013	Approved
0.6562	Remote Similarity	NPD8034	Phase 2
0.6562	Remote Similarity	NPD8035	Phase 2
0.6562	Remote Similarity	NPD5284	Approved
0.6562	Remote Similarity	NPD5281	Approved
0.6559	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6098	Approved
0.6556	Remote Similarity	NPD4139	Approved
0.6556	Remote Similarity	NPD4692	Approved
0.6548	Remote Similarity	NPD4747	Approved
0.6542	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD8297	Approved
0.6538	Remote Similarity	NPD5701	Approved
0.6531	Remote Similarity	NPD5695	Phase 3
0.6512	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5169	Approved
0.6509	Remote Similarity	NPD5248	Approved
0.6509	Remote Similarity	NPD5250	Approved
0.6509	Remote Similarity	NPD5251	Approved
0.6509	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5249	Phase 3
0.6509	Remote Similarity	NPD5247	Approved
0.6509	Remote Similarity	NPD5135	Approved
0.6509	Remote Similarity	NPD4634	Approved
0.65	Remote Similarity	NPD5696	Approved
0.6484	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD4269	Approved
0.6476	Remote Similarity	NPD5128	Approved
0.6452	Remote Similarity	NPD1696	Phase 3

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