NPASS Compound

Structure

NPC474634 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 -5.9105 -1.1456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2163 -0.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7734 -2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5436 -3.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9594 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 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 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7515 -2.4328 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.2868 -4.0800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7297 -2.6407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 16 29 1 0 0 0 0 17 28 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 19 26 1 0 0 0 0 20 30 1 1 0 0 0 21 27 1 1 0 0 0 22 25 1 0 0 0 0 22 27 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 1 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.36
Volume:	491.143
LogP:	4.407
LogD:	4.328
LogS:	-4.333
# Rotatable Bonds:	6
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	4.863
Fsp3:	0.929
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:	-4.683
MDCK Permeability:	1.922373667184729e-05
Pgp-inhibitor:	0.538
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	95.11954498291016%
Volume Distribution (VD):	0.938
Pgp-substrate:	1.7420610189437866%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.554
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	9.397
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.25
Skin Sensitization:	0.5
Carcinogencity:	0.136
Eye Corrosion:	0.004
Eye Irritation:	0.058
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC474634

Natural Product ID:	NPC474634
*Common Name:**	Ergost-5-Ene-3Beta,7Alpha,24,28-Tetraol
IUPAC Name:	(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroxy-5-(hydroxymethyl)-6-methylheptan-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:
Standard InCHIKey:	IOUFZQNFNWOOHO-ZNCVFNLDSA-N
Standard InCHI:	InChI=1S/C28H48O4/c1-17(2)28(32,16-29)13-8-18(3)21-6-7-22-25-23(10-12-27(21,22)5)26(4)11-9-20(30)14-19(26)15-24(25)31/h15,17-18,20-25,29-32H,6-14,16H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-,28?/m1/s1
SMILES:	CC(C)C(CCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477739
PubChem CID:	44584670
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001110] Tetrahydroxy bile acids, alcohols 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
NPO11093	Pseudobersama mossambicensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479381]
NPO11093	Pseudobersama mossambicensis	Species	Meliaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	1.0	ug ml-1	PMID[507547]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	100.0	ug ml-1	PMID[507547]

☑ 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 NPC474634 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	156
0.1-0.2	1305
0.2-0.3	5180
0.3-0.4	15072
0.4-0.5	8551
0.5-0.6	5961
0.6-0.7	4752
0.7-0.8	1382
0.8-0.85	199
0.85-0.9	81
0.9-0.95	54
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC185568
0.9494	High Similarity	NPC317458
0.9487	High Similarity	NPC264245
0.9481	High Similarity	NPC28862
0.9481	High Similarity	NPC47982
0.9481	High Similarity	NPC143182
0.9481	High Similarity	NPC81306
0.9481	High Similarity	NPC109546
0.9481	High Similarity	NPC328714
0.9481	High Similarity	NPC84694
0.939	High Similarity	NPC474668
0.9375	High Similarity	NPC205845
0.9367	High Similarity	NPC101462
0.9367	High Similarity	NPC49964
0.9359	High Similarity	NPC234193
0.9359	High Similarity	NPC241290
0.9359	High Similarity	NPC209944
0.9359	High Similarity	NPC164840
0.9351	High Similarity	NPC474216
0.925	High Similarity	NPC475789
0.9241	High Similarity	NPC47761
0.9241	High Similarity	NPC23852
0.9241	High Similarity	NPC209620
0.9231	High Similarity	NPC30986
0.9231	High Similarity	NPC209430
0.9221	High Similarity	NPC318495
0.9221	High Similarity	NPC198968
0.9221	High Similarity	NPC155986
0.9146	High Similarity	NPC6391
0.9146	High Similarity	NPC293287
0.9146	High Similarity	NPC261266
0.9146	High Similarity	NPC152808
0.9125	High Similarity	NPC189972
0.9125	High Similarity	NPC30166
0.9125	High Similarity	NPC50964
0.9103	High Similarity	NPC83351
0.9103	High Similarity	NPC473943
0.9103	High Similarity	NPC167891
0.9091	High Similarity	NPC321016
0.9091	High Similarity	NPC321381
0.9091	High Similarity	NPC244488
0.9091	High Similarity	NPC107059
0.9091	High Similarity	NPC247325
0.9059	High Similarity	NPC97404
0.9059	High Similarity	NPC41554
0.9048	High Similarity	NPC477606
0.9048	High Similarity	NPC470361
0.9036	High Similarity	NPC149224
0.9024	High Similarity	NPC266511
0.9024	High Similarity	NPC274448
0.9	High Similarity	NPC7505
0.9	High Similarity	NPC474683
0.9	High Similarity	NPC474759
0.9	High Similarity	NPC474752
0.9	High Similarity	NPC474731
0.9	High Similarity	NPC82986
0.9	High Similarity	NPC474531
0.8961	High Similarity	NPC28657
0.8961	High Similarity	NPC134847
0.8961	High Similarity	NPC285893
0.8961	High Similarity	NPC304309
0.8961	High Similarity	NPC162742
0.8961	High Similarity	NPC22105
0.8961	High Similarity	NPC230301
0.8961	High Similarity	NPC288035
0.8961	High Similarity	NPC136188
0.8941	High Similarity	NPC204188
0.8941	High Similarity	NPC80561
0.8941	High Similarity	NPC3345
0.8941	High Similarity	NPC291484
0.8941	High Similarity	NPC11216
0.8941	High Similarity	NPC329596
0.8929	High Similarity	NPC67872
0.8929	High Similarity	NPC133588
0.8902	High Similarity	NPC238485
0.8902	High Similarity	NPC474047
0.8889	High Similarity	NPC218616
0.8889	High Similarity	NPC296701
0.8889	High Similarity	NPC87489
0.8875	High Similarity	NPC236112
0.8875	High Similarity	NPC13554
0.8861	High Similarity	NPC87604
0.8861	High Similarity	NPC477522
0.8846	High Similarity	NPC240604
0.8846	High Similarity	NPC300324
0.8846	High Similarity	NPC113733
0.881	High Similarity	NPC470620
0.8795	High Similarity	NPC157257
0.8795	High Similarity	NPC318390
0.878	High Similarity	NPC207013
0.8734	High Similarity	NPC34019
0.8721	High Similarity	NPC295668
0.8718	High Similarity	NPC257347
0.8718	High Similarity	NPC471723
0.8718	High Similarity	NPC141071
0.8706	High Similarity	NPC280556
0.869	High Similarity	NPC477604
0.869	High Similarity	NPC94462
0.8675	High Similarity	NPC231310
0.8675	High Similarity	NPC470077
0.8659	High Similarity	NPC202389
0.8659	High Similarity	NPC470049
0.8659	High Similarity	NPC470614
0.8659	High Similarity	NPC1272
0.8652	High Similarity	NPC288970
0.8642	High Similarity	NPC236237
0.8642	High Similarity	NPC22403
0.8642	High Similarity	NPC26117
0.8642	High Similarity	NPC322313
0.8642	High Similarity	NPC102253
0.8636	High Similarity	NPC477605
0.8625	High Similarity	NPC76931
0.8625	High Similarity	NPC18603
0.8625	High Similarity	NPC275910
0.8625	High Similarity	NPC307965
0.8625	High Similarity	NPC285761
0.8625	High Similarity	NPC477514
0.8608	High Similarity	NPC477925
0.8608	High Similarity	NPC274079
0.8608	High Similarity	NPC129165
0.8608	High Similarity	NPC315261
0.8608	High Similarity	NPC189883
0.8608	High Similarity	NPC134330
0.8608	High Similarity	NPC96319
0.8605	High Similarity	NPC32830
0.859	High Similarity	NPC469534
0.859	High Similarity	NPC469533
0.859	High Similarity	NPC469593
0.8571	High Similarity	NPC470360
0.8554	High Similarity	NPC470384
0.8554	High Similarity	NPC82623
0.8554	High Similarity	NPC320548
0.8537	High Similarity	NPC6707
0.8537	High Similarity	NPC470383
0.8523	High Similarity	NPC310013
0.8519	High Similarity	NPC1319
0.8519	High Similarity	NPC80530
0.8519	High Similarity	NPC273410
0.85	High Similarity	NPC477924
0.85	High Similarity	NPC470758
0.85	High Similarity	NPC91594
0.85	High Similarity	NPC214570
0.85	High Similarity	NPC470711
0.8481	Intermediate Similarity	NPC477923
0.8481	Intermediate Similarity	NPC66566
0.8471	Intermediate Similarity	NPC125399
0.8471	Intermediate Similarity	NPC299068
0.8462	Intermediate Similarity	NPC471799
0.8462	Intermediate Similarity	NPC474140
0.8452	Intermediate Similarity	NPC124172
0.8452	Intermediate Similarity	NPC15534
0.8444	Intermediate Similarity	NPC72204
0.8442	Intermediate Similarity	NPC34834
0.8434	Intermediate Similarity	NPC7988
0.8434	Intermediate Similarity	NPC5985
0.8427	Intermediate Similarity	NPC127718
0.8427	Intermediate Similarity	NPC292793
0.8427	Intermediate Similarity	NPC65402
0.8409	Intermediate Similarity	NPC275671
0.8395	Intermediate Similarity	NPC244385
0.8395	Intermediate Similarity	NPC138621
0.8395	Intermediate Similarity	NPC476314
0.8395	Intermediate Similarity	NPC167037
0.8395	Intermediate Similarity	NPC301707
0.8395	Intermediate Similarity	NPC6978
0.8391	Intermediate Similarity	NPC105495
0.8391	Intermediate Similarity	NPC146554
0.8375	Intermediate Similarity	NPC237460
0.8375	Intermediate Similarity	NPC91573
0.8375	Intermediate Similarity	NPC265588
0.8375	Intermediate Similarity	NPC202642
0.8375	Intermediate Similarity	NPC470362
0.8375	Intermediate Similarity	NPC73875
0.8375	Intermediate Similarity	NPC470749
0.8375	Intermediate Similarity	NPC46160
0.8372	Intermediate Similarity	NPC90652
0.8354	Intermediate Similarity	NPC471797
0.8354	Intermediate Similarity	NPC27395
0.8354	Intermediate Similarity	NPC476366
0.8354	Intermediate Similarity	NPC201048
0.8354	Intermediate Similarity	NPC329090
0.8353	Intermediate Similarity	NPC474349
0.8353	Intermediate Similarity	NPC474189
0.8353	Intermediate Similarity	NPC471224
0.8352	Intermediate Similarity	NPC476893
0.8333	Intermediate Similarity	NPC8774
0.8333	Intermediate Similarity	NPC470558
0.8333	Intermediate Similarity	NPC134481
0.8333	Intermediate Similarity	NPC476894
0.8315	Intermediate Similarity	NPC474736
0.8313	Intermediate Similarity	NPC70927
0.8313	Intermediate Similarity	NPC476646
0.8313	Intermediate Similarity	NPC320525
0.8295	Intermediate Similarity	NPC48010
0.8276	Intermediate Similarity	NPC471952
0.8276	Intermediate Similarity	NPC470417
0.8261	Intermediate Similarity	NPC476895
0.8256	Intermediate Similarity	NPC139724
0.8256	Intermediate Similarity	NPC474970
0.8256	Intermediate Similarity	NPC24277

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 NPC474634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1489
0.2-0.3	4204
0.3-0.4	2316
0.4-0.5	548
0.5-0.6	169
0.6-0.7	182
0.7-0.8	78
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8961	High Similarity	NPD6942	Approved
0.8961	High Similarity	NPD7339	Approved
0.8642	High Similarity	NPD7525	Registered
0.8608	High Similarity	NPD6933	Approved
0.8608	High Similarity	NPD3701	Clinical (unspecified phase)
0.8588	High Similarity	NPD4751	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6924	Approved
0.8354	Intermediate Similarity	NPD6926	Approved
0.8235	Intermediate Similarity	NPD4786	Approved
0.8193	Intermediate Similarity	NPD6930	Phase 2
0.8193	Intermediate Similarity	NPD6931	Approved
0.8161	Intermediate Similarity	NPD7524	Approved
0.8125	Intermediate Similarity	NPD4784	Approved
0.8125	Intermediate Similarity	NPD4785	Approved
0.8118	Intermediate Similarity	NPD6695	Phase 3
0.8101	Intermediate Similarity	NPD4243	Approved
0.8072	Intermediate Similarity	NPD6929	Approved
0.8023	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3667	Approved
0.7976	Intermediate Similarity	NPD7514	Phase 3
0.7952	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7152	Approved
0.7875	Intermediate Similarity	NPD7150	Approved
0.7875	Intermediate Similarity	NPD7151	Approved
0.7848	Intermediate Similarity	NPD6922	Approved
0.7848	Intermediate Similarity	NPD6923	Approved
0.7831	Intermediate Similarity	NPD6925	Approved
0.7831	Intermediate Similarity	NPD5776	Phase 2
0.7765	Intermediate Similarity	NPD7332	Phase 2
0.7765	Intermediate Similarity	NPD4748	Discontinued
0.7753	Intermediate Similarity	NPD7750	Discontinued
0.775	Intermediate Similarity	NPD7144	Approved
0.775	Intermediate Similarity	NPD7143	Approved
0.7738	Intermediate Similarity	NPD7145	Approved
0.7727	Intermediate Similarity	NPD6893	Approved
0.7674	Intermediate Similarity	NPD6902	Approved
0.7647	Intermediate Similarity	NPD7645	Phase 2
0.7619	Intermediate Similarity	NPD6932	Approved
0.759	Intermediate Similarity	NPD8264	Approved
0.759	Intermediate Similarity	NPD4190	Phase 3
0.759	Intermediate Similarity	NPD5275	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7558	Intermediate Similarity	NPD7509	Discontinued
0.7527	Intermediate Similarity	NPD6399	Phase 3
0.7471	Intermediate Similarity	NPD6898	Phase 1
0.7444	Intermediate Similarity	NPD3618	Phase 1
0.7442	Intermediate Similarity	NPD4195	Approved
0.7442	Intermediate Similarity	NPD6683	Phase 2
0.7419	Intermediate Similarity	NPD7087	Discontinued
0.7419	Intermediate Similarity	NPD6079	Approved
0.7416	Intermediate Similarity	NPD3665	Phase 1
0.7416	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3666	Approved
0.7416	Intermediate Similarity	NPD3668	Phase 3
0.7407	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4753	Phase 2
0.7391	Intermediate Similarity	NPD6051	Approved
0.734	Intermediate Similarity	NPD4202	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD4755	Approved
0.7196	Intermediate Similarity	NPD7115	Discovery
0.7191	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.7129	Intermediate Similarity	NPD5141	Approved
0.7113	Intermediate Similarity	NPD5222	Approved
0.7113	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5221	Approved
0.7113	Intermediate Similarity	NPD4697	Phase 3
0.7071	Intermediate Similarity	NPD4700	Approved
0.7071	Intermediate Similarity	NPD5286	Approved
0.7071	Intermediate Similarity	NPD4696	Approved
0.7071	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD5279	Phase 3
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD5173	Approved
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7033	Intermediate Similarity	NPD4197	Approved
0.701	Intermediate Similarity	NPD5210	Approved
0.701	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD4159	Approved
0.7	Intermediate Similarity	NPD5223	Approved
0.697	Remote Similarity	NPD4225	Approved
0.6962	Remote Similarity	NPD368	Approved
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5226	Approved
0.6931	Remote Similarity	NPD4633	Approved
0.6931	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4788	Approved
0.6893	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD7128	Approved
0.6893	Remote Similarity	NPD6675	Approved
0.6893	Remote Similarity	NPD6402	Approved
0.6882	Remote Similarity	NPD4689	Approved
0.6882	Remote Similarity	NPD4693	Phase 3
0.6882	Remote Similarity	NPD4688	Approved
0.6882	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD4138	Approved
0.6882	Remote Similarity	NPD4519	Discontinued
0.6882	Remote Similarity	NPD5205	Approved
0.6882	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD7515	Phase 2
0.6863	Remote Similarity	NPD5175	Approved
0.6863	Remote Similarity	NPD4754	Approved
0.6863	Remote Similarity	NPD5174	Approved
0.6792	Remote Similarity	NPD4634	Approved
0.6771	Remote Similarity	NPD7136	Phase 2
0.6762	Remote Similarity	NPD7320	Approved
0.6762	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD6899	Approved
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5737	Approved
0.6737	Remote Similarity	NPD4722	Approved
0.6737	Remote Similarity	NPD4723	Approved
0.6737	Remote Similarity	NPD6672	Approved
0.6731	Remote Similarity	NPD4767	Approved
0.6731	Remote Similarity	NPD4768	Approved
0.6706	Remote Similarity	NPD4787	Phase 1
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD5280	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD4694	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.6698	Remote Similarity	NPD6372	Approved
0.6698	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6637	Remote Similarity	NPD8033	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6634	Remote Similarity	NPD5696	Approved
0.6634	Remote Similarity	NPD5290	Discontinued
0.6623	Remote Similarity	NPD342	Phase 1
0.6607	Remote Similarity	NPD7516	Approved
0.6606	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD4730	Approved
0.6604	Remote Similarity	NPD4729	Approved
0.6604	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6593	Remote Similarity	NPD4695	Discontinued
0.6593	Remote Similarity	NPD4820	Approved
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6869	Approved
0.6574	Remote Similarity	NPD6649	Approved
0.6574	Remote Similarity	NPD6847	Approved
0.6574	Remote Similarity	NPD8130	Phase 1
0.6574	Remote Similarity	NPD6650	Approved
0.6574	Remote Similarity	NPD6617	Approved
0.6571	Remote Similarity	NPD6640	Phase 3
0.6566	Remote Similarity	NPD7748	Approved
0.6562	Remote Similarity	NPD6903	Approved
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5362	Discontinued
0.6559	Remote Similarity	NPD5332	Approved
0.6559	Remote Similarity	NPD5331	Approved
0.6556	Remote Similarity	NPD3617	Approved
0.6549	Remote Similarity	NPD8294	Approved
0.6549	Remote Similarity	NPD8377	Approved
0.6542	Remote Similarity	NPD6012	Approved
0.6542	Remote Similarity	NPD6013	Approved
0.6542	Remote Similarity	NPD6014	Approved
0.6531	Remote Similarity	NPD5284	Approved
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD8034	Phase 2
0.6531	Remote Similarity	NPD5281	Approved
0.6526	Remote Similarity	NPD6098	Approved
0.6522	Remote Similarity	NPD4692	Approved
0.6522	Remote Similarity	NPD4139	Approved
0.6522	Remote Similarity	NPD4790	Discontinued
0.6514	Remote Similarity	NPD6882	Approved
0.6495	Remote Similarity	NPD6080	Approved
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6904	Approved
0.6491	Remote Similarity	NPD8335	Approved
0.6491	Remote Similarity	NPD7503	Approved
0.6491	Remote Similarity	NPD8378	Approved
0.6491	Remote Similarity	NPD8296	Approved
0.6491	Remote Similarity	NPD8380	Approved
0.6491	Remote Similarity	NPD8379	Approved
0.6481	Remote Similarity	NPD5169	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