NPASS Compound

Structure

NPC473567 OpenBabel07101718182D 44 48 0 0 1 0 0 0 0 0999 V2000 -6.1809 6.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1664 4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8282 5.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5191 5.0032 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4680 7.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7989 8.3916 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1590 6.6974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.1883 4.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 2 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8793 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4670 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8208 8.1837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4670 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1883 0.7399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 5 41 1 0 0 0 0 6 42 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 35 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 22 1 0 0 0 0 16 34 1 0 0 0 0 17 23 1 0 0 0 0 17 43 1 0 0 0 0 19 2 1 6 0 0 0 19 25 1 0 0 0 0 20 44 1 6 0 0 0 21 22 1 0 0 0 0 21 32 1 0 0 0 0 22 36 1 6 0 0 0 23 28 1 0 0 0 0 23 37 1 6 0 0 0 24 32 1 6 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 6 0 0 0 26 27 1 0 0 0 0 26 38 1 6 0 0 0 27 30 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 41 1 1 0 0 0 29 31 1 0 0 0 0 29 42 1 6 0 0 0 30 33 1 6 0 0 0 30 34 1 0 0 0 0 31 43 1 0 0 0 0 31 44 1 1 0 0 0 32 3 1 6 0 0 0 33 4 1 6 0 0 0 34 40 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.39
Volume:	636.467
LogP:	1.955
LogD:	1.399
LogS:	-3.616
# Rotatable Bonds:	9
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	5.892
Fsp3:	0.882
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.535
MDCK Permeability:	6.533171108458191e-05
Pgp-inhibitor:	0.837
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.816
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	78.06511688232422%
Volume Distribution (VD):	0.582
Pgp-substrate:	7.419025897979736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.508
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	0.925
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.515
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.148
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC473567

Natural Product ID:	NPC473567
*Common Name:**	3-O-Beta-D-(2,3-Di-O-Methyl-Beta-Xylopyranosyl)-22E-27-Nor-24-Methyl-5Alpha-Cholesta-4,22-Diene-3Beta,6Beta,8,15R,16Beta,26-Hexaol
IUPAC Name:	(3S,6R,8S,9R,10R,13R,14S,15R,16R,17R)-3-[(2S,3R,4S,5R)-5-hydroxy-3,4-dimethoxyoxan-2-yl]oxy-17-[(E,2R)-7-hydroxy-5-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,6,7,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-6,8,15,16-tetrol
Synonyms:
Standard InCHIKey:	FNZWIYAOZVPPCK-RTKWNISRSA-N
Standard InCHI:	InChI=1S/C34H56O10/c1-18(11-14-35)7-8-19(2)25-26(38)27(39)30-33(25,4)13-10-24-32(3)12-9-20(15-21(32)22(36)16-34(24,30)40)44-31-29(42-6)28(41-5)23(37)17-43-31/h7-8,15,18-20,22-31,35-40H,9-14,16-17H2,1-6H3/b8-7+/t18?,19-,20+,22-,23-,24-,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+/m1/s1
SMILES:	CC(CCO)C=CC(C)C1C(C(C2C1(CCC3C2(CC(C4=CC(CCC34C)OC5C(C(C(CO5)O)OC)OC)O)O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445795
PubChem CID:	11614270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO8018	Henricia leviuscula	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499320]
NPO8018	Henricia leviuscula	Species	Echinasteridae	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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	=	100.0	%	PMID[511098]
NPT27	Others	Unspecified		HC50	=	8.0	10'-5M	PMID[511098]

☑ 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 NPC473567 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	267
0.1-0.2	1776
0.2-0.3	5188
0.3-0.4	11374
0.4-0.5	10624
0.5-0.6	6416
0.6-0.7	4306
0.7-0.8	2162
0.8-0.85	439
0.85-0.9	125
0.9-0.95	18
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC216595
0.9429	High Similarity	NPC103627
0.9429	High Similarity	NPC65155
0.9429	High Similarity	NPC191439
0.9429	High Similarity	NPC170974
0.9333	High Similarity	NPC473318
0.9333	High Similarity	NPC473328
0.9333	High Similarity	NPC28844
0.9327	High Similarity	NPC33053
0.9252	High Similarity	NPC477050
0.9252	High Similarity	NPC231797
0.9252	High Similarity	NPC475354
0.9159	High Similarity	NPC208189
0.9159	High Similarity	NPC65034
0.9135	High Similarity	NPC75608
0.9135	High Similarity	NPC93352
0.9048	High Similarity	NPC472898
0.9048	High Similarity	NPC472899
0.9048	High Similarity	NPC472900
0.9048	High Similarity	NPC26798
0.9029	High Similarity	NPC21568
0.9029	High Similarity	NPC285231
0.8991	High Similarity	NPC51154
0.8981	High Similarity	NPC13190
0.8972	High Similarity	NPC472901
0.8972	High Similarity	NPC250089
0.8972	High Similarity	NPC128133
0.8972	High Similarity	NPC14630
0.8972	High Similarity	NPC157530
0.8962	High Similarity	NPC231340
0.8962	High Similarity	NPC226642
0.8952	High Similarity	NPC312774
0.8899	High Similarity	NPC112274
0.8879	High Similarity	NPC472896
0.8879	High Similarity	NPC472897
0.8879	High Similarity	NPC235824
0.8868	High Similarity	NPC473923
0.8868	High Similarity	NPC474569
0.8868	High Similarity	NPC473476
0.8868	High Similarity	NPC242748
0.8857	High Similarity	NPC473198
0.8857	High Similarity	NPC471886
0.8857	High Similarity	NPC471885
0.8857	High Similarity	NPC471887
0.8857	High Similarity	NPC471888
0.8846	High Similarity	NPC47566
0.8846	High Similarity	NPC4831
0.8846	High Similarity	NPC88000
0.8846	High Similarity	NPC309425
0.8846	High Similarity	NPC470434
0.8846	High Similarity	NPC129372
0.8846	High Similarity	NPC160734
0.8846	High Similarity	NPC472023
0.8818	High Similarity	NPC469348
0.8818	High Similarity	NPC469347
0.8818	High Similarity	NPC307642
0.8807	High Similarity	NPC197231
0.8807	High Similarity	NPC473021
0.8807	High Similarity	NPC472987
0.8785	High Similarity	NPC473469
0.8774	High Similarity	NPC475365
0.8774	High Similarity	NPC470885
0.8774	High Similarity	NPC221562
0.8774	High Similarity	NPC187400
0.8762	High Similarity	NPC471482
0.8762	High Similarity	NPC37207
0.8762	High Similarity	NPC136816
0.8762	High Similarity	NPC300399
0.875	High Similarity	NPC469942
0.875	High Similarity	NPC474418
0.875	High Similarity	NPC93883
0.875	High Similarity	NPC471355
0.875	High Similarity	NPC87250
0.875	High Similarity	NPC142066
0.875	High Similarity	NPC471354
0.875	High Similarity	NPC243196
0.875	High Similarity	NPC471353
0.875	High Similarity	NPC34390
0.875	High Similarity	NPC100048
0.875	High Similarity	NPC244402
0.875	High Similarity	NPC196429
0.875	High Similarity	NPC473200
0.875	High Similarity	NPC471351
0.875	High Similarity	NPC158344
0.875	High Similarity	NPC309034
0.875	High Similarity	NPC157376
0.875	High Similarity	NPC7341
0.875	High Similarity	NPC50305
0.875	High Similarity	NPC99728
0.875	High Similarity	NPC20979
0.875	High Similarity	NPC77319
0.875	High Similarity	NPC84987
0.875	High Similarity	NPC27507
0.875	High Similarity	NPC473852
0.875	High Similarity	NPC203862
0.875	High Similarity	NPC476690
0.8739	High Similarity	NPC11548
0.8738	High Similarity	NPC240372
0.8727	High Similarity	NPC19888
0.8716	High Similarity	NPC141433
0.8704	High Similarity	NPC476539
0.8704	High Similarity	NPC476540
0.8704	High Similarity	NPC476541
0.8704	High Similarity	NPC80210
0.8704	High Similarity	NPC38376
0.8704	High Similarity	NPC476538
0.8692	High Similarity	NPC474015
0.8684	High Similarity	NPC475629
0.8684	High Similarity	NPC475556
0.8679	High Similarity	NPC286969
0.8679	High Similarity	NPC31907
0.8679	High Similarity	NPC155010
0.8679	High Similarity	NPC472252
0.8679	High Similarity	NPC8039
0.8679	High Similarity	NPC211879
0.8679	High Similarity	NPC473124
0.8679	High Similarity	NPC473123
0.8679	High Similarity	NPC157659
0.8679	High Similarity	NPC473020
0.8679	High Similarity	NPC245280
0.8679	High Similarity	NPC16520
0.8679	High Similarity	NPC213190
0.8679	High Similarity	NPC189852
0.8679	High Similarity	NPC131479
0.8679	High Similarity	NPC475701
0.8679	High Similarity	NPC120123
0.8679	High Similarity	NPC114874
0.8673	High Similarity	NPC475403
0.8673	High Similarity	NPC160888
0.8673	High Similarity	NPC10366
0.8673	High Similarity	NPC83287
0.8661	High Similarity	NPC99620
0.8661	High Similarity	NPC477029
0.8661	High Similarity	NPC193382
0.8661	High Similarity	NPC148965
0.8661	High Similarity	NPC5311
0.8661	High Similarity	NPC477030
0.8661	High Similarity	NPC310341
0.8661	High Similarity	NPC199428
0.8654	High Similarity	NPC234287
0.8654	High Similarity	NPC158088
0.8654	High Similarity	NPC280825
0.8641	High Similarity	NPC90583
0.8624	High Similarity	NPC42482
0.8624	High Similarity	NPC306131
0.8624	High Similarity	NPC195116
0.8624	High Similarity	NPC477026
0.8624	High Similarity	NPC476835
0.8624	High Similarity	NPC475670
0.8624	High Similarity	NPC70204
0.8624	High Similarity	NPC285253
0.8624	High Similarity	NPC221110
0.8624	High Similarity	NPC180459
0.8624	High Similarity	NPC40440
0.8624	High Similarity	NPC477027
0.8611	High Similarity	NPC190395
0.8609	High Similarity	NPC173555
0.8609	High Similarity	NPC314535
0.8609	High Similarity	NPC40749
0.8598	High Similarity	NPC474464
0.8598	High Similarity	NPC273879
0.8598	High Similarity	NPC473127
0.8598	High Similarity	NPC110656
0.8598	High Similarity	NPC203354
0.8598	High Similarity	NPC165033
0.8596	High Similarity	NPC5883
0.8596	High Similarity	NPC32177
0.8596	High Similarity	NPC236973
0.8596	High Similarity	NPC473633
0.8596	High Similarity	NPC469756
0.8596	High Similarity	NPC30483
0.8596	High Similarity	NPC29639
0.8596	High Similarity	NPC44899
0.8596	High Similarity	NPC292467
0.8596	High Similarity	NPC55532
0.8596	High Similarity	NPC476085
0.8596	High Similarity	NPC470897
0.8596	High Similarity	NPC304260
0.8585	High Similarity	NPC312553
0.8585	High Similarity	NPC159036
0.8585	High Similarity	NPC288694
0.8585	High Similarity	NPC272015
0.8584	High Similarity	NPC152615
0.8571	High Similarity	NPC69576
0.8571	High Similarity	NPC471633
0.8571	High Similarity	NPC31354
0.8571	High Similarity	NPC64348
0.8571	High Similarity	NPC84949
0.8571	High Similarity	NPC91497
0.8559	High Similarity	NPC42171
0.8559	High Similarity	NPC475312
0.8558	High Similarity	NPC243728
0.8558	High Similarity	NPC473890
0.8545	High Similarity	NPC472717
0.8534	High Similarity	NPC264336
0.8532	High Similarity	NPC7213
0.8522	High Similarity	NPC107607
0.8522	High Similarity	NPC475136
0.8522	High Similarity	NPC474466
0.8522	High Similarity	NPC50689

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 NPC473567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	1865
0.2-0.3	4116
0.3-0.4	1955
0.4-0.5	553
0.5-0.6	249
0.6-0.7	157
0.7-0.8	23
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8673	High Similarity	NPD7327	Approved
0.8673	High Similarity	NPD7328	Approved
0.8609	High Similarity	NPD8380	Approved
0.8609	High Similarity	NPD8379	Approved
0.8609	High Similarity	NPD8296	Approved
0.8609	High Similarity	NPD8378	Approved
0.8609	High Similarity	NPD8335	Approved
0.8596	High Similarity	NPD7516	Approved
0.8522	High Similarity	NPD8294	Approved
0.8522	High Similarity	NPD8377	Approved
0.8448	Intermediate Similarity	NPD8033	Approved
0.8448	Intermediate Similarity	NPD7503	Approved
0.8017	Intermediate Similarity	NPD7507	Approved
0.7967	Intermediate Similarity	NPD7319	Approved
0.7788	Intermediate Similarity	NPD6412	Phase 2
0.7692	Intermediate Similarity	NPD8133	Approved
0.748	Intermediate Similarity	NPD6370	Approved
0.746	Intermediate Similarity	NPD7736	Approved
0.7414	Intermediate Similarity	NPD6686	Approved
0.7339	Intermediate Similarity	NPD8171	Discontinued
0.7317	Intermediate Similarity	NPD6054	Approved
0.7257	Intermediate Similarity	NPD7640	Approved
0.7257	Intermediate Similarity	NPD7639	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7203	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7524	Approved
0.7177	Intermediate Similarity	NPD6059	Approved
0.7168	Intermediate Similarity	NPD7638	Approved
0.712	Intermediate Similarity	NPD6015	Approved
0.712	Intermediate Similarity	NPD6016	Approved
0.712	Intermediate Similarity	NPD8517	Approved
0.712	Intermediate Similarity	NPD8513	Phase 3
0.712	Intermediate Similarity	NPD8516	Approved
0.712	Intermediate Similarity	NPD8515	Approved
0.7087	Intermediate Similarity	NPD7492	Approved
0.7075	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7115	Discovery
0.7063	Intermediate Similarity	NPD5988	Approved
0.704	Intermediate Similarity	NPD6319	Approved
0.7037	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6616	Approved
0.7025	Intermediate Similarity	NPD8297	Approved
0.7025	Intermediate Similarity	NPD6882	Approved
0.7019	Intermediate Similarity	NPD7525	Registered
0.6981	Remote Similarity	NPD6695	Phase 3
0.6977	Remote Similarity	NPD7078	Approved
0.697	Remote Similarity	NPD8449	Approved
0.6935	Remote Similarity	NPD6009	Approved
0.6917	Remote Similarity	NPD8450	Suspended
0.6897	Remote Similarity	NPD4159	Approved
0.6881	Remote Similarity	NPD7750	Discontinued
0.6875	Remote Similarity	NPD8328	Phase 3
0.6875	Remote Similarity	NPD6067	Discontinued
0.6829	Remote Similarity	NPD4632	Approved
0.6809	Remote Similarity	NPD7625	Phase 1
0.68	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6051	Approved
0.6752	Remote Similarity	NPD5344	Discontinued
0.6723	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4634	Approved
0.6698	Remote Similarity	NPD6928	Phase 2
0.6698	Remote Similarity	NPD7514	Phase 3
0.6698	Remote Similarity	NPD6930	Phase 2
0.6698	Remote Similarity	NPD6931	Approved
0.6695	Remote Similarity	NPD5211	Phase 2
0.6695	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD6899	Approved
0.6694	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5697	Approved
0.6604	Remote Similarity	NPD6929	Approved
0.6604	Remote Similarity	NPD7645	Phase 2
0.6585	Remote Similarity	NPD7102	Approved
0.6585	Remote Similarity	NPD7290	Approved
0.6585	Remote Similarity	NPD6883	Approved
0.6585	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5141	Approved
0.6581	Remote Similarity	NPD4225	Approved
0.6557	Remote Similarity	NPD7320	Approved
0.6557	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7332	Phase 2
0.6538	Remote Similarity	NPD7339	Approved
0.6538	Remote Similarity	NPD6942	Approved
0.6532	Remote Similarity	NPD6617	Approved
0.6532	Remote Similarity	NPD6847	Approved
0.6532	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD4696	Approved
0.6525	Remote Similarity	NPD5286	Approved
0.6525	Remote Similarity	NPD5285	Approved
0.6509	Remote Similarity	NPD7145	Approved
0.6504	Remote Similarity	NPD6013	Approved
0.6504	Remote Similarity	NPD6014	Approved
0.6504	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD4755	Approved
0.6491	Remote Similarity	NPD7637	Suspended
0.6491	Remote Similarity	NPD7087	Discontinued
0.6489	Remote Similarity	NPD7604	Phase 2
0.6481	Remote Similarity	NPD6902	Approved
0.6475	Remote Similarity	NPD5701	Approved
0.6466	Remote Similarity	NPD8074	Phase 3
0.6462	Remote Similarity	NPD5983	Phase 2
0.6442	Remote Similarity	NPD4784	Approved
0.6442	Remote Similarity	NPD4785	Approved
0.6441	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4202	Approved
0.6423	Remote Similarity	NPD6011	Approved
0.6417	Remote Similarity	NPD5226	Approved
0.6417	Remote Similarity	NPD4633	Approved
0.6417	Remote Similarity	NPD5224	Approved
0.6417	Remote Similarity	NPD5225	Approved
0.6415	Remote Similarity	NPD6925	Approved
0.6415	Remote Similarity	NPD6932	Approved
0.6415	Remote Similarity	NPD5776	Phase 2
0.6408	Remote Similarity	NPD4243	Approved
0.6396	Remote Similarity	NPD6893	Approved
0.6391	Remote Similarity	NPD6336	Discontinued
0.6387	Remote Similarity	NPD6648	Approved
0.6387	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD6084	Phase 2
0.6356	Remote Similarity	NPD6083	Phase 2
0.6349	Remote Similarity	NPD6053	Discontinued
0.6341	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5223	Approved
0.6324	Remote Similarity	NPD5956	Approved
0.6321	Remote Similarity	NPD6933	Approved
0.6293	Remote Similarity	NPD6399	Phase 3
0.629	Remote Similarity	NPD4730	Approved
0.629	Remote Similarity	NPD4729	Approved
0.627	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7741	Discontinued
0.626	Remote Similarity	NPD4767	Approved
0.626	Remote Similarity	NPD6640	Phase 3
0.626	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD4748	Discontinued
0.6207	Remote Similarity	NPD6079	Approved
0.6207	Remote Similarity	NPD8034	Phase 2
0.6207	Remote Similarity	NPD8035	Phase 2
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5250	Approved
0.6183	Remote Similarity	NPD7100	Approved
0.6183	Remote Similarity	NPD7101	Approved
0.6182	Remote Similarity	NPD6898	Phase 1
0.6174	Remote Similarity	NPD4753	Phase 2
0.6174	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4786	Approved
0.6149	Remote Similarity	NPD7799	Discontinued
0.6147	Remote Similarity	NPD4195	Approved
0.6147	Remote Similarity	NPD6683	Phase 2
0.6132	Remote Similarity	NPD6924	Approved
0.6132	Remote Similarity	NPD6926	Approved
0.6121	Remote Similarity	NPD7838	Discovery
0.6121	Remote Similarity	NPD3168	Discontinued
0.6107	Remote Similarity	NPD6335	Approved
0.6102	Remote Similarity	NPD7748	Approved
0.6098	Remote Similarity	NPD4754	Approved
0.609	Remote Similarity	NPD6921	Approved
0.6083	Remote Similarity	NPD7902	Approved
0.6077	Remote Similarity	NPD6274	Approved
0.6075	Remote Similarity	NPD5275	Approved
0.6075	Remote Similarity	NPD4190	Phase 3
0.6075	Remote Similarity	NPD8264	Approved
0.6063	Remote Similarity	NPD6371	Approved
0.6058	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3618	Phase 1
0.605	Remote Similarity	NPD5210	Approved
0.605	Remote Similarity	NPD4629	Approved
0.605	Remote Similarity	NPD7991	Discontinued
0.605	Remote Similarity	NPD5695	Phase 3
0.6045	Remote Similarity	NPD5126	Approved
0.6045	Remote Similarity	NPD5125	Phase 3
0.6033	Remote Similarity	NPD5696	Approved
0.6032	Remote Similarity	NPD5128	Approved
0.6031	Remote Similarity	NPD6317	Approved
0.6018	Remote Similarity	NPD3133	Approved
0.6018	Remote Similarity	NPD3666	Approved
0.6018	Remote Similarity	NPD3665	Phase 1
0.6016	Remote Similarity	NPD5217	Approved
0.6016	Remote Similarity	NPD5216	Approved
0.6016	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD5222	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