NPASS Compound

Structure

NPC475226 OpenBabel07101718192D 44 48 0 0 1 0 0 0 0 0999 V2000 3.5491 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0491 1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8867 -3.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 -3.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0491 1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 -2.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -4.0148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 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 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 8 40 1 0 0 0 0 9 17 2 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 41 1 0 0 0 0 12 21 1 0 0 0 0 13 23 1 0 0 0 0 13 26 1 0 0 0 0 14 24 1 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 41 1 0 0 0 0 16 32 1 0 0 0 0 16 35 2 0 0 0 0 17 31 1 0 0 0 0 18 21 1 0 0 0 0 18 27 2 0 0 0 0 19 36 2 0 0 0 0 19 42 1 0 0 0 0 21 20 1 6 0 0 0 22 12 1 1 0 0 0 22 27 1 0 0 0 0 22 43 1 0 0 0 0 23 33 1 6 0 0 0 23 34 1 0 0 0 0 24 32 1 6 0 0 0 24 37 1 0 0 0 0 25 33 1 6 0 0 0 25 44 1 0 0 0 0 26 38 2 0 0 0 0 26 40 1 0 0 0 0 27 34 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 42 1 6 0 0 0 29 32 1 1 0 0 0 29 33 1 0 0 0 0 30 34 1 6 0 0 0 30 43 1 0 0 0 0 31 39 2 0 0 0 0 31 44 1 0 0 0 0 32 5 1 1 0 0 0 33 6 1 1 0 0 0 34 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.29
Volume:	620.648
LogP:	2.508
LogD:	1.531
LogS:	-4.51
# Rotatable Bonds:	10
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	5.657
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.177
MDCK Permeability:	7.769562944304198e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.111
20% Bioavailability (F20%):	0.818
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.824
Plasma Protein Binding (PPB):	73.57040405273438%
Volume Distribution (VD):	2.539
Pgp-substrate:	13.875256538391113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.193
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	6.768
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.658
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.324
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.348
Carcinogencity:	0.035
Eye Corrosion:	0.005
Eye Irritation:	0.018
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC475226

Natural Product ID:	NPC475226
*Common Name:**	Ohchinolal
IUPAC Name:	n.a.
Synonyms:	Ohchinolal
Standard InCHIKey:	JOVDKZRXWAATEG-HLIKQWNHSA-N
Standard InCHI:	InChI=1S/C34H44O10/c1-9-17(2)31(39)44-25-14-24(37)32(5,16-35)29-28(42-19(4)36)30-34(7,23(33(25,29)6)13-26(38)40-8)27-18(3)21(12-22(27)43-30)20-10-11-41-15-20/h9-11,15-16,21-25,28-30,37H,12-14H2,1-8H3/b17-9+/t21-,22-,23+,24-,25+,28-,29+,30-,32-,33+,34-/m1/s1
SMILES:	COC(=O)C[C@H]1[C@@]2(C)[C@@H](OC(=O)/C(=C/C)/C)C[C@H]([C@@]([C@@H]2[C@H]([C@@H]2[C@@]1(C)C1=C(C)[C@@H](C[C@H]1O2)c1ccoc1)OC(=O)C)(C)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501420
PubChem CID:	44584372
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	Activity	=	100.0	%	PMID[525820]

☑ 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 NPC475226 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	328
0.1-0.2	1207
0.2-0.3	2950
0.3-0.4	4987
0.4-0.5	9931
0.5-0.6	10496
0.6-0.7	10135
0.7-0.8	2115
0.8-0.85	281
0.85-0.9	211
0.9-0.95	53
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC475066
0.9669	High Similarity	NPC214495
0.9669	High Similarity	NPC470119
0.9605	High Similarity	NPC472671
0.9481	High Similarity	NPC470792
0.943	High Similarity	NPC475641
0.943	High Similarity	NPC475237
0.9404	High Similarity	NPC29695
0.9404	High Similarity	NPC322546
0.9404	High Similarity	NPC308205
0.9404	High Similarity	NPC182427
0.9333	High Similarity	NPC472654
0.9299	High Similarity	NPC307781
0.9299	High Similarity	NPC472670
0.9286	High Similarity	NPC470118
0.9286	High Similarity	NPC197137
0.9276	High Similarity	NPC472672
0.9216	High Similarity	NPC34421
0.9216	High Similarity	NPC98206
0.9216	High Similarity	NPC253201
0.9216	High Similarity	NPC237259
0.9216	High Similarity	NPC302054
0.9205	High Similarity	NPC195325
0.9187	High Similarity	NPC285227
0.9177	High Similarity	NPC472141
0.9167	High Similarity	NPC470789
0.9161	High Similarity	NPC472776
0.9161	High Similarity	NPC472777
0.9161	High Similarity	NPC472778
0.9156	High Similarity	NPC155939
0.9156	High Similarity	NPC296807
0.9156	High Similarity	NPC141538
0.9125	High Similarity	NPC118086
0.9103	High Similarity	NPC475967
0.9085	High Similarity	NPC18135
0.9085	High Similarity	NPC116717
0.9079	High Similarity	NPC125182
0.9079	High Similarity	NPC69647
0.9073	High Similarity	NPC255414
0.9062	High Similarity	NPC472673
0.9051	High Similarity	NPC472139
0.9038	High Similarity	NPC299038
0.9038	High Similarity	NPC469847
0.9026	High Similarity	NPC268905
0.9026	High Similarity	NPC469503
0.8987	High Similarity	NPC472771
0.8987	High Similarity	NPC200782
0.8954	High Similarity	NPC470791
0.8954	High Similarity	NPC470790
0.8954	High Similarity	NPC471001
0.8944	High Similarity	NPC472652
0.8944	High Similarity	NPC271235
0.8931	High Similarity	NPC472773
0.8931	High Similarity	NPC472669
0.8931	High Similarity	NPC471168
0.8924	High Similarity	NPC472653
0.891	High Similarity	NPC92979
0.891	High Similarity	NPC476262
0.8903	High Similarity	NPC476201
0.8903	High Similarity	NPC33938
0.8896	High Similarity	NPC156189
0.8896	High Similarity	NPC470997
0.8896	High Similarity	NPC196846
0.8889	High Similarity	NPC470995
0.8889	High Similarity	NPC471007
0.8882	High Similarity	NPC472764
0.8882	High Similarity	NPC472651
0.8875	High Similarity	NPC62692
0.8875	High Similarity	NPC61967
0.8875	High Similarity	NPC27541
0.8875	High Similarity	NPC126984
0.8874	High Similarity	NPC251865
0.8868	High Similarity	NPC82851
0.8868	High Similarity	NPC471166
0.8868	High Similarity	NPC472668
0.8868	High Similarity	NPC471167
0.8855	High Similarity	NPC470938
0.8846	High Similarity	NPC282445
0.8841	High Similarity	NPC94763
0.8839	High Similarity	NPC291150
0.8831	High Similarity	NPC234494
0.8827	High Similarity	NPC472765
0.8827	High Similarity	NPC472766
0.8824	High Similarity	NPC216755
0.8824	High Similarity	NPC221809
0.8824	High Similarity	NPC471174
0.882	High Similarity	NPC97574
0.882	High Similarity	NPC93172
0.882	High Similarity	NPC470875
0.8816	High Similarity	NPC5676
0.8812	High Similarity	NPC469846
0.8812	High Similarity	NPC134254
0.8812	High Similarity	NPC39986
0.8812	High Similarity	NPC165218
0.8812	High Similarity	NPC302369
0.881	High Similarity	NPC105395
0.881	High Similarity	NPC242068
0.881	High Similarity	NPC247563
0.8805	High Similarity	NPC191828
0.8797	High Similarity	NPC261597
0.8797	High Similarity	NPC472772
0.8797	High Similarity	NPC36655
0.8797	High Similarity	NPC167142
0.8795	High Similarity	NPC11062
0.879	High Similarity	NPC44675
0.879	High Similarity	NPC214541
0.879	High Similarity	NPC469336
0.8782	High Similarity	NPC75906
0.878	High Similarity	NPC469848
0.8774	High Similarity	NPC5180
0.8773	High Similarity	NPC82602
0.8773	High Similarity	NPC472659
0.8765	High Similarity	NPC100333
0.8765	High Similarity	NPC476861
0.8765	High Similarity	NPC472774
0.8765	High Similarity	NPC476850
0.8765	High Similarity	NPC472775
0.8765	High Similarity	NPC310572
0.8758	High Similarity	NPC123088
0.8758	High Similarity	NPC470999
0.8758	High Similarity	NPC470182
0.8758	High Similarity	NPC469849
0.8758	High Similarity	NPC276551
0.875	High Similarity	NPC329938
0.875	High Similarity	NPC188649
0.875	High Similarity	NPC472767
0.875	High Similarity	NPC69028
0.8742	High Similarity	NPC121158
0.8742	High Similarity	NPC307383
0.8727	High Similarity	NPC471632
0.8727	High Similarity	NPC236004
0.8727	High Similarity	NPC471437
0.8726	High Similarity	NPC178932
0.8726	High Similarity	NPC57998
0.8712	High Similarity	NPC471397
0.8712	High Similarity	NPC160651
0.8712	High Similarity	NPC327922
0.8704	High Similarity	NPC121995
0.8704	High Similarity	NPC214600
0.8701	High Similarity	NPC250228
0.8696	High Similarity	NPC292389
0.8696	High Similarity	NPC288602
0.8696	High Similarity	NPC283209
0.8696	High Similarity	NPC285567
0.8696	High Similarity	NPC88841
0.8696	High Similarity	NPC469338
0.8696	High Similarity	NPC477405
0.8688	High Similarity	NPC335761
0.8684	High Similarity	NPC223415
0.8679	High Similarity	NPC88007
0.8679	High Similarity	NPC45101
0.8679	High Similarity	NPC249021
0.8679	High Similarity	NPC187149
0.8679	High Similarity	NPC194499
0.8679	High Similarity	NPC195954
0.8675	High Similarity	NPC469633
0.8671	High Similarity	NPC264943
0.8671	High Similarity	NPC35000
0.8662	High Similarity	NPC470996
0.8662	High Similarity	NPC471002
0.8654	High Similarity	NPC476122
0.865	High Similarity	NPC478179
0.865	High Similarity	NPC173516
0.865	High Similarity	NPC472282
0.8642	High Similarity	NPC476857
0.8642	High Similarity	NPC271657
0.8642	High Similarity	NPC470940
0.8642	High Similarity	NPC476856
0.8642	High Similarity	NPC476858
0.8634	High Similarity	NPC68848
0.8634	High Similarity	NPC5079
0.8634	High Similarity	NPC211777
0.8634	High Similarity	NPC207978
0.8634	High Similarity	NPC18986
0.8627	High Similarity	NPC476944
0.8625	High Similarity	NPC84349
0.8625	High Similarity	NPC474611
0.8623	High Similarity	NPC478177
0.8614	High Similarity	NPC469576
0.8609	High Similarity	NPC67003
0.8608	High Similarity	NPC30222
0.8606	High Similarity	NPC159232
0.8606	High Similarity	NPC294512
0.8606	High Similarity	NPC169299
0.8606	High Similarity	NPC160818
0.8599	High Similarity	NPC471000
0.859	High Similarity	NPC470998
0.8589	High Similarity	NPC478178
0.858	High Similarity	NPC419
0.858	High Similarity	NPC198047
0.858	High Similarity	NPC234660
0.858	High Similarity	NPC224394
0.858	High Similarity	NPC51568
0.858	High Similarity	NPC476197
0.858	High Similarity	NPC663
0.8571	High Similarity	NPC25255
0.8571	High Similarity	NPC477402
0.8571	High Similarity	NPC41182
0.8562	High Similarity	NPC476946
0.8562	High Similarity	NPC243577

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 NPC475226 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	882
0.2-0.3	2093
0.3-0.4	2640
0.4-0.5	1965
0.5-0.6	976
0.6-0.7	285
0.7-0.8	32
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD5761	Phase 2
0.8671	High Similarity	NPD5760	Phase 2
0.8314	Intermediate Similarity	NPD8434	Phase 2
0.7714	Intermediate Similarity	NPD6764	Approved
0.7714	Intermediate Similarity	NPD6765	Approved
0.7692	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7542	Intermediate Similarity	NPD6785	Approved
0.7542	Intermediate Similarity	NPD6784	Approved
0.7456	Intermediate Similarity	NPD7819	Suspended
0.7399	Intermediate Similarity	NPD8127	Discontinued
0.7318	Intermediate Similarity	NPD6559	Discontinued
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7253	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6273	Approved
0.7225	Intermediate Similarity	NPD7075	Discontinued
0.7222	Intermediate Similarity	NPD8404	Phase 2
0.7202	Intermediate Similarity	NPD920	Approved
0.7178	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD5494	Approved
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7095	Intermediate Similarity	NPD7799	Discontinued
0.7095	Intermediate Similarity	NPD3818	Discontinued
0.7093	Intermediate Similarity	NPD6801	Discontinued
0.7086	Intermediate Similarity	NPD919	Approved
0.7083	Intermediate Similarity	NPD2532	Approved
0.7083	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2534	Approved
0.7083	Intermediate Similarity	NPD2533	Approved
0.7069	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6232	Discontinued
0.7049	Intermediate Similarity	NPD8312	Approved
0.7049	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD6799	Approved
0.7018	Intermediate Similarity	NPD3226	Approved
0.7011	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3817	Phase 2
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.6994	Remote Similarity	NPD37	Approved
0.6989	Remote Similarity	NPD6234	Discontinued
0.6982	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4380	Phase 2
0.6971	Remote Similarity	NPD3882	Suspended
0.697	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6004	Phase 3
0.697	Remote Similarity	NPD6005	Phase 3
0.697	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6002	Phase 3
0.6968	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2799	Discontinued
0.694	Remote Similarity	NPD7685	Pre-registration
0.6936	Remote Similarity	NPD7411	Suspended
0.6932	Remote Similarity	NPD3749	Approved
0.6932	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5402	Approved
0.691	Remote Similarity	NPD1247	Approved
0.6909	Remote Similarity	NPD1551	Phase 2
0.6906	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7228	Approved
0.6897	Remote Similarity	NPD1934	Approved
0.6886	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7768	Phase 2
0.6868	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5762	Approved
0.6867	Remote Similarity	NPD2346	Discontinued
0.6867	Remote Similarity	NPD5763	Approved
0.6867	Remote Similarity	NPD1471	Phase 3
0.6864	Remote Similarity	NPD7236	Approved
0.6845	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3926	Phase 2
0.6833	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7074	Phase 3
0.6828	Remote Similarity	NPD8407	Phase 2
0.6826	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7458	Discontinued
0.6807	Remote Similarity	NPD2796	Approved
0.6802	Remote Similarity	NPD5403	Approved
0.6796	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6166	Phase 2
0.6796	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7497	Discontinued
0.6786	Remote Similarity	NPD2800	Approved
0.6786	Remote Similarity	NPD1243	Approved
0.6784	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5401	Approved
0.6776	Remote Similarity	NPD7054	Approved
0.6772	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6832	Phase 2
0.6768	Remote Similarity	NPD6355	Discontinued
0.6766	Remote Similarity	NPD2344	Approved
0.6763	Remote Similarity	NPD7239	Suspended
0.6761	Remote Similarity	NPD2801	Approved
0.6757	Remote Similarity	NPD7240	Approved
0.6757	Remote Similarity	NPD8368	Discontinued
0.6755	Remote Similarity	NPD8150	Discontinued
0.675	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7033	Discontinued
0.6746	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4110	Phase 3
0.6739	Remote Similarity	NPD7472	Approved
0.6726	Remote Similarity	NPD1549	Phase 2
0.6725	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6959	Discontinued
0.672	Remote Similarity	NPD7808	Phase 3
0.672	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1608	Approved
0.6707	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD2935	Discontinued
0.6705	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2313	Discontinued
0.6685	Remote Similarity	NPD7229	Phase 3
0.6685	Remote Similarity	NPD7315	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1465	Phase 2
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7251	Discontinued
0.6647	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD8032	Phase 2
0.6646	Remote Similarity	NPD5647	Approved
0.6627	Remote Similarity	NPD6653	Approved
0.6613	Remote Similarity	NPD6797	Phase 2
0.6608	Remote Similarity	NPD2309	Approved
0.6607	Remote Similarity	NPD6100	Approved
0.6607	Remote Similarity	NPD6099	Approved
0.6593	Remote Similarity	NPD5710	Approved
0.6593	Remote Similarity	NPD5711	Approved
0.659	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5735	Approved
0.6552	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.655	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7003	Approved
0.6548	Remote Similarity	NPD3748	Approved
0.6548	Remote Similarity	NPD1510	Phase 2
0.6541	Remote Similarity	NPD3751	Discontinued
0.6533	Remote Similarity	NPD7435	Discontinued
0.6532	Remote Similarity	NPD1511	Approved
0.6527	Remote Similarity	NPD1607	Approved
0.6524	Remote Similarity	NPD5953	Discontinued
0.6519	Remote Similarity	NPD17	Approved
0.6512	Remote Similarity	NPD6190	Approved
0.651	Remote Similarity	NPD8361	Approved
0.651	Remote Similarity	NPD8360	Approved
0.651	Remote Similarity	NPD8435	Approved
0.6509	Remote Similarity	NPD2438	Suspended
0.6506	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1240	Approved
0.6505	Remote Similarity	NPD7286	Phase 2
0.6503	Remote Similarity	NPD6808	Phase 2
0.6503	Remote Similarity	NPD3787	Discontinued
0.6497	Remote Similarity	NPD7028	Phase 2
0.6488	Remote Similarity	NPD7097	Phase 1
0.6485	Remote Similarity	NPD3764	Approved
0.6467	Remote Similarity	NPD230	Phase 1
0.6467	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6385	Approved
0.6461	Remote Similarity	NPD6386	Approved
0.6457	Remote Similarity	NPD1512	Approved
0.6456	Remote Similarity	NPD7930	Approved
0.6453	Remote Similarity	NPD8151	Discontinued
0.6453	Remote Similarity	NPD8166	Discontinued
0.645	Remote Similarity	NPD7680	Approved
0.645	Remote Similarity	NPD7697	Approved
0.645	Remote Similarity	NPD7696	Phase 3
0.645	Remote Similarity	NPD7698	Approved
0.6446	Remote Similarity	NPD6663	Approved
0.6445	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5353	Approved
0.6429	Remote Similarity	NPD6651	Approved
0.6429	Remote Similarity	NPD7907	Approved
0.6424	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7874	Approved
0.6418	Remote Similarity	NPD7870	Phase 2
0.6418	Remote Similarity	NPD7871	Phase 2
0.6417	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1778	Approved
0.6409	Remote Similarity	NPD7058	Phase 2
0.6409	Remote Similarity	NPD7057	Phase 3
0.6398	Remote Similarity	NPD3972	Approved
0.6398	Remote Similarity	NPD9717	Approved
0.6396	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.639	Remote Similarity	NPD7783	Phase 2
0.639	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6798	Discontinued
0.6386	Remote Similarity	NPD7999	Approved
0.6386	Remote Similarity	NPD3268	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