NPASS Compound

Structure

NPC472772 OpenBabel07101718182D 39 43 0 0 1 0 0 0 0 0999 V2000 1.0249 0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7352 -2.8011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3553 -2.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1486 -2.3042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2922 -4.4015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4097 -1.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3879 -1.4095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0832 -2.9453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0517 -0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 1.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2187 0.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1589 -0.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1178 -1.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3052 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4659 -2.0214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5176 -1.2144 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2929 -0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6920 -3.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5731 1.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1589 -1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5731 -1.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4392 0.2929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2247 -1.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.4142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5731 -0.2071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7071 0.2929 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1093 -1.7467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3093 -4.6625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5731 2.7929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0249 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6834 -3.6081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8879 -0.5435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5091 -1.0839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 1.2929 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 35 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 36 1 0 0 0 0 10 17 1 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 36 1 0 0 0 0 14 23 1 0 0 0 0 14 29 1 1 0 0 0 15 30 2 0 0 0 0 15 37 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 17 27 1 6 0 0 0 18 26 1 0 0 0 0 18 37 1 1 0 0 0 19 27 1 1 0 0 0 19 39 1 0 0 0 0 20 31 2 0 0 0 0 20 35 1 0 0 0 0 21 32 2 0 0 0 0 21 38 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 27 1 1 0 0 0 23 33 2 0 0 0 0 24 28 1 6 0 0 0 24 34 1 0 0 0 0 25 28 1 6 0 0 0 25 38 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 6 0 0 0 29 12 1 6 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.25
Volume:	539.441
LogP:	3.046
LogD:	1.509
LogS:	-3.828
# Rotatable Bonds:	6
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	6.575
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
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:	-5.322
MDCK Permeability:	9.31E-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.819
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.683
Plasma Protein Binding (PPB):	66.26%
Volume Distribution (VD):	0.706
Pgp-substrate:	34.21%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.381

ADMET: Excretion

Clearance (CL):	10.804
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.736
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.282
Carcinogencity:	0.237
Eye Corrosion:	0.877
Eye Irritation:	0.032
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC472772

Natural Product ID:	NPC472772
*Common Name:**	GIFDVMDUUPUHDE-ZBHBTJMJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GIFDVMDUUPUHDE-ZBHBTJMJSA-N
Standard InCHI:	InChI=1S/C29H38O10/c1-14-23(33)22-24(34)28(6)25(16-8-9-36-13-16)38-21(32)12-29(14,28)39-19-11-18(37-15(2)30)26(3,4)17(27(19,22)5)10-20(31)35-7/h8-9,13-14,17-19,22,24-25,34H,10-12H2,1-7H3/t14-,17-,18+,19-,22+,24-,25-,27+,28-,29-/m0/s1
SMILES:	CC1C(=O)C2C(C3(C1(CC(=O)OC3C4=COC=C4)OC5C2(C(C(C(C5)OC(=O)C)(C)C)CC(=O)OC)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582101
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids 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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[543919]

☑ 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 NPC472772 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	360
0.1-0.2	1486
0.2-0.3	3275
0.3-0.4	6025
0.4-0.5	10772
0.5-0.6	10234
0.6-0.7	8813
0.7-0.8	1384
0.8-0.85	233
0.85-0.9	101
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC472771
0.9737	High Similarity	NPC472773
0.96	High Similarity	NPC469336
0.9548	High Similarity	NPC472774
0.9548	High Similarity	NPC472775
0.9533	High Similarity	NPC178932
0.9474	High Similarity	NPC167142
0.9467	High Similarity	NPC469503
0.9423	High Similarity	NPC476853
0.9416	High Similarity	NPC472767
0.9404	High Similarity	NPC282445
0.9355	High Similarity	NPC477405
0.9346	High Similarity	NPC249021
0.9342	High Similarity	NPC264943
0.9333	High Similarity	NPC469335
0.9333	High Similarity	NPC196864
0.9333	High Similarity	NPC477404
0.9333	High Similarity	NPC159927
0.9295	High Similarity	NPC276551
0.9295	High Similarity	NPC476857
0.9295	High Similarity	NPC476858
0.9295	High Similarity	NPC476856
0.929	High Similarity	NPC69028
0.9262	High Similarity	NPC470941
0.9241	High Similarity	NPC471397
0.9236	High Similarity	NPC470875
0.9236	High Similarity	NPC23387
0.9231	High Similarity	NPC292389
0.9231	High Similarity	NPC469338
0.9226	High Similarity	NPC25255
0.9226	High Similarity	NPC477402
0.9221	High Similarity	NPC45101
0.9216	High Similarity	NPC469850
0.9211	High Similarity	NPC75906
0.9205	High Similarity	NPC476122
0.9177	High Similarity	NPC173516
0.9177	High Similarity	NPC476850
0.9177	High Similarity	NPC476861
0.9177	High Similarity	NPC472764
0.9177	High Similarity	NPC472282
0.9172	High Similarity	NPC476860
0.9172	High Similarity	NPC469849
0.9172	High Similarity	NPC123088
0.9172	High Similarity	NPC470940
0.9167	High Similarity	NPC193798
0.9167	High Similarity	NPC200782
0.9167	High Similarity	NPC263432
0.9167	High Similarity	NPC329938
0.9167	High Similarity	NPC82851
0.9161	High Similarity	NPC477403
0.9161	High Similarity	NPC237155
0.9156	High Similarity	NPC204663
0.9119	High Similarity	NPC472766
0.9119	High Similarity	NPC160651
0.9119	High Similarity	NPC472765
0.9114	High Similarity	NPC149945
0.9108	High Similarity	NPC419
0.9108	High Similarity	NPC134254
0.9108	High Similarity	NPC39986
0.9108	High Similarity	NPC302369
0.9097	High Similarity	NPC195131
0.9091	High Similarity	NPC35000
0.9085	High Similarity	NPC476201
0.9079	High Similarity	NPC156189
0.906	High Similarity	NPC476944
0.9057	High Similarity	NPC472651
0.9045	High Similarity	NPC5079
0.9045	High Similarity	NPC470939
0.9038	High Similarity	NPC475967
0.9038	High Similarity	NPC474611
0.9032	High Similarity	NPC41880
0.9026	High Similarity	NPC30222
0.9026	High Similarity	NPC57998
0.9013	High Similarity	NPC195325
0.9013	High Similarity	NPC472654
0.9	High Similarity	NPC472652
0.8994	High Similarity	NPC121995
0.8987	High Similarity	NPC663
0.8987	High Similarity	NPC224394
0.8987	High Similarity	NPC165218
0.8987	High Similarity	NPC234660
0.8987	High Similarity	NPC51568
0.8987	High Similarity	NPC476197
0.8981	High Similarity	NPC472653
0.8981	High Similarity	NPC335761
0.8974	High Similarity	NPC299038
0.8974	High Similarity	NPC472283
0.8968	High Similarity	NPC476262
0.894	High Similarity	NPC262198
0.8931	High Similarity	NPC470182
0.8926	High Similarity	NPC121158
0.8924	High Similarity	NPC6326
0.8924	High Similarity	NPC188649
0.8924	High Similarity	NPC18986
0.8924	High Similarity	NPC207978
0.8917	High Similarity	NPC307383
0.8917	High Similarity	NPC140952
0.891	High Similarity	NPC469485
0.891	High Similarity	NPC263265
0.891	High Similarity	NPC126723
0.8889	High Similarity	NPC211625
0.8889	High Similarity	NPC470791
0.8889	High Similarity	NPC125182
0.8889	High Similarity	NPC470790
0.8889	High Similarity	NPC69647
0.8882	High Similarity	NPC250228
0.8882	High Similarity	NPC271235
0.8882	High Similarity	NPC221809
0.8882	High Similarity	NPC255414
0.8875	High Similarity	NPC93172
0.8875	High Similarity	NPC97574
0.8874	High Similarity	NPC41182
0.8868	High Similarity	NPC88841
0.8868	High Similarity	NPC288602
0.8867	High Similarity	NPC243577
0.8861	High Similarity	NPC470789
0.8854	High Similarity	NPC36655
0.8854	High Similarity	NPC173544
0.8854	High Similarity	NPC304692
0.8854	High Similarity	NPC286722
0.8854	High Similarity	NPC472776
0.8854	High Similarity	NPC472777
0.8854	High Similarity	NPC81405
0.8854	High Similarity	NPC472778
0.8854	High Similarity	NPC261597
0.8846	High Similarity	NPC75310
0.8846	High Similarity	NPC92979
0.8846	High Similarity	NPC281258
0.8846	High Similarity	NPC214541
0.8846	High Similarity	NPC44675
0.8831	High Similarity	NPC212257
0.882	High Similarity	NPC270312
0.8816	High Similarity	NPC346
0.8812	High Similarity	NPC271657
0.8808	High Similarity	NPC142113
0.8808	High Similarity	NPC251865
0.8805	High Similarity	NPC68848
0.8805	High Similarity	NPC96443
0.8805	High Similarity	NPC290400
0.8805	High Similarity	NPC117986
0.8805	High Similarity	NPC211777
0.8797	High Similarity	NPC475226
0.8797	High Similarity	NPC475295
0.8797	High Similarity	NPC473473
0.8792	High Similarity	NPC67003
0.879	High Similarity	NPC104736
0.879	High Similarity	NPC60973
0.879	High Similarity	NPC209364
0.879	High Similarity	NPC107646
0.8784	High Similarity	NPC476943
0.8782	High Similarity	NPC114880
0.878	High Similarity	NPC471437
0.8774	High Similarity	NPC18135
0.8758	High Similarity	NPC478178
0.8758	High Similarity	NPC216755
0.8758	High Similarity	NPC475779
0.8758	High Similarity	NPC471174
0.8758	High Similarity	NPC472141
0.875	High Similarity	NPC472139
0.875	High Similarity	NPC198047
0.875	High Similarity	NPC5676
0.8742	High Similarity	NPC287559
0.8742	High Similarity	NPC191828
0.8742	High Similarity	NPC305016
0.8742	High Similarity	NPC475381
0.8742	High Similarity	NPC267632
0.8734	High Similarity	NPC195954
0.8734	High Similarity	NPC88007
0.8734	High Similarity	NPC187149
0.8734	High Similarity	NPC194499
0.8734	High Similarity	NPC475066
0.8718	High Similarity	NPC476939
0.8718	High Similarity	NPC476940
0.8718	High Similarity	NPC475777
0.8712	High Similarity	NPC82602
0.8704	High Similarity	NPC473766
0.8704	High Similarity	NPC473753
0.8704	High Similarity	NPC476224
0.8696	High Similarity	NPC56358
0.8688	High Similarity	NPC18347
0.8688	High Similarity	NPC149896
0.8679	High Similarity	NPC262872
0.8675	High Similarity	NPC478177
0.8667	High Similarity	NPC471632
0.8659	High Similarity	NPC285227
0.8659	High Similarity	NPC160818
0.8659	High Similarity	NPC169299
0.8654	High Similarity	NPC272590
0.865	High Similarity	NPC296558
0.8649	High Similarity	NPC46896
0.8642	High Similarity	NPC214600
0.8634	High Similarity	NPC283209
0.8634	High Similarity	NPC469846
0.8634	High Similarity	NPC472669
0.8634	High Similarity	NPC285567
0.8618	High Similarity	NPC476946
0.8616	High Similarity	NPC197137
0.8599	High Similarity	NPC472672
0.8599	High Similarity	NPC268905
0.8598	High Similarity	NPC470995

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 NPC472772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	1068
0.2-0.3	2177
0.3-0.4	2684
0.4-0.5	1890
0.5-0.6	779
0.6-0.7	224
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8726	High Similarity	NPD5761	Phase 2
0.8726	High Similarity	NPD5760	Phase 2
0.8363	Intermediate Similarity	NPD8434	Phase 2
0.7952	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7819	Suspended
0.7657	Intermediate Similarity	NPD6764	Approved
0.7657	Intermediate Similarity	NPD6765	Approved
0.759	Intermediate Similarity	NPD7411	Suspended
0.756	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6784	Approved
0.7486	Intermediate Similarity	NPD6785	Approved
0.7471	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD3749	Approved
0.747	Intermediate Similarity	NPD3226	Approved
0.7455	Intermediate Similarity	NPD920	Approved
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7346	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6599	Discontinued
0.7314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5494	Approved
0.7235	Intermediate Similarity	NPD6801	Discontinued
0.7229	Intermediate Similarity	NPD2533	Approved
0.7229	Intermediate Similarity	NPD2534	Approved
0.7229	Intermediate Similarity	NPD2532	Approved
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD4380	Phase 2
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5844	Phase 1
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6273	Approved
0.7178	Intermediate Similarity	NPD1549	Phase 2
0.7175	Intermediate Similarity	NPD7473	Discontinued
0.7172	Intermediate Similarity	NPD8404	Phase 2
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD2796	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7135	Intermediate Similarity	NPD3818	Discontinued
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7066	Intermediate Similarity	NPD6799	Approved
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7052	Intermediate Similarity	NPD5402	Approved
0.7052	Intermediate Similarity	NPD3817	Phase 2
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7045	Intermediate Similarity	NPD1247	Approved
0.7035	Intermediate Similarity	NPD1934	Approved
0.703	Intermediate Similarity	NPD2800	Approved
0.703	Intermediate Similarity	NPD1243	Approved
0.7029	Intermediate Similarity	NPD919	Approved
0.7024	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD7236	Approved
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7033	Discontinued
0.6988	Remote Similarity	NPD3750	Approved
0.697	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7074	Phase 3
0.6941	Remote Similarity	NPD5403	Approved
0.6937	Remote Similarity	NPD3268	Approved
0.6937	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2313	Discontinued
0.6936	Remote Similarity	NPD37	Approved
0.6927	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6166	Phase 2
0.6927	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5401	Approved
0.6918	Remote Similarity	NPD6832	Phase 2
0.6914	Remote Similarity	NPD4966	Approved
0.6914	Remote Similarity	NPD4965	Approved
0.6914	Remote Similarity	NPD4967	Phase 2
0.6914	Remote Similarity	NPD3882	Suspended
0.691	Remote Similarity	NPD7229	Phase 3
0.6909	Remote Similarity	NPD2344	Approved
0.6906	Remote Similarity	NPD7054	Approved
0.6901	Remote Similarity	NPD7239	Suspended
0.689	Remote Similarity	NPD1510	Phase 2
0.689	Remote Similarity	NPD3748	Approved
0.6886	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8150	Discontinued
0.6868	Remote Similarity	NPD7472	Approved
0.686	Remote Similarity	NPD7458	Discontinued
0.6851	Remote Similarity	NPD7799	Discontinued
0.6848	Remote Similarity	NPD2935	Discontinued
0.6848	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7435	Discontinued
0.6816	Remote Similarity	NPD5711	Approved
0.6816	Remote Similarity	NPD6808	Phase 2
0.6816	Remote Similarity	NPD5710	Approved
0.68	Remote Similarity	NPD2801	Approved
0.6793	Remote Similarity	NPD7251	Discontinued
0.6778	Remote Similarity	NPD3926	Phase 2
0.6774	Remote Similarity	NPD8407	Phase 2
0.6768	Remote Similarity	NPD1607	Approved
0.676	Remote Similarity	NPD7199	Phase 2
0.6758	Remote Similarity	NPD7228	Approved
0.6758	Remote Similarity	NPD3751	Discontinued
0.6757	Remote Similarity	NPD7808	Phase 3
0.6752	Remote Similarity	NPD1608	Approved
0.6748	Remote Similarity	NPD1240	Approved
0.6746	Remote Similarity	NPD2309	Approved
0.6744	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6234	Discontinued
0.6739	Remote Similarity	NPD6797	Phase 2
0.6739	Remote Similarity	NPD5953	Discontinued
0.673	Remote Similarity	NPD3266	Approved
0.673	Remote Similarity	NPD3267	Approved
0.6728	Remote Similarity	NPD3764	Approved
0.6722	Remote Similarity	NPD3787	Discontinued
0.6721	Remote Similarity	NPD7286	Phase 2
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1465	Phase 2
0.6703	Remote Similarity	NPD8368	Discontinued
0.6703	Remote Similarity	NPD7685	Pre-registration
0.6701	Remote Similarity	NPD8285	Discontinued
0.6687	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD8032	Phase 2
0.6686	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7697	Approved
0.6646	Remote Similarity	NPD4140	Approved
0.6632	Remote Similarity	NPD4287	Approved
0.6632	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7097	Phase 1
0.6626	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2797	Approved
0.6617	Remote Similarity	NPD7874	Approved
0.6617	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7871	Phase 2
0.6616	Remote Similarity	NPD7870	Phase 2
0.6613	Remote Similarity	NPD7240	Approved
0.661	Remote Similarity	NPD8455	Phase 2
0.6606	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6355	Discontinued
0.6606	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5124	Phase 1
0.6593	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1512	Approved
0.6584	Remote Similarity	NPD2798	Approved
0.6582	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7497	Discontinued
0.6561	Remote Similarity	NPD17	Approved
0.6554	Remote Similarity	NPD6844	Discontinued
0.6545	Remote Similarity	NPD4307	Phase 2
0.6545	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD9717	Approved
0.6541	Remote Similarity	NPD3972	Approved
0.6538	Remote Similarity	NPD7907	Approved
0.6536	Remote Similarity	NPD7057	Phase 3
0.6536	Remote Similarity	NPD7058	Phase 2
0.6533	Remote Similarity	NPD8319	Approved
0.6533	Remote Similarity	NPD8320	Phase 1
0.6522	Remote Similarity	NPD4665	Approved
0.6522	Remote Similarity	NPD4111	Phase 1
0.6522	Remote Similarity	NPD1203	Approved
0.6517	Remote Similarity	NPD7701	Phase 2
0.6515	Remote Similarity	NPD6823	Phase 2
0.6509	Remote Similarity	NPD5763	Approved
0.6509	Remote Similarity	NPD5762	Approved
0.6506	Remote Similarity	NPD447	Suspended
0.6502	Remote Similarity	NPD7783	Phase 2
0.6502	Remote Similarity	NPD7801	Approved
0.6502	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5889	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