NPASS Compound

Structure

NPC240521 OpenBabel07101718272D 27 32 0 0 1 0 0 0 0 0999 V2000 5.8448 1.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8448 2.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1860 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3448 1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3448 1.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8448 2.8442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3200 -1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 2.7872 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 10 2 0 0 0 0 2 11 2 0 0 0 0 2 13 1 0 0 0 0 3 11 1 0 0 0 0 3 15 1 0 0 0 0 4 12 2 0 0 0 0 4 19 1 0 0 0 0 5 16 2 0 0 0 0 5 17 1 0 0 0 0 6 18 2 0 0 0 0 6 20 1 0 0 0 0 7 10 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 9 25 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 14 8 1 6 0 0 0 14 21 1 0 0 0 0 15 10 1 1 0 0 0 15 26 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 18 27 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 13 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.11
Volume:	354.72
LogP:	4.238
LogD:	3.153
LogS:	-6.057
# Rotatable Bonds:	2
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	4.114
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.134
MDCK Permeability:	1.991043973248452e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	97.88573455810547%
Volume Distribution (VD):	0.781
Pgp-substrate:	2.616046667098999%

ADMET: Metabolism

CYP1A2-inhibitor:	0.41
CYP1A2-substrate:	0.72
CYP2C19-inhibitor:	0.832
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.622
CYP2D6-inhibitor:	0.869
CYP2D6-substrate:	0.828
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	10.984
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.988
Rat Oral Acute Toxicity:	0.717
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.422
Carcinogencity:	0.759
Eye Corrosion:	0.003
Eye Irritation:	0.382
Respiratory Toxicity:	0.751

Download Data

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

Natural Product: NPC240521

Natural Product ID:	NPC240521
*Common Name:**	KSESTLPJESZHFG-ZSDSOXJFSA-N
IUPAC Name:	n.a.
Synonyms:	(2'R)-4'-Hydroxyemoroidocarpan
Standard InCHIKey:	KSESTLPJESZHFG-ZSDSOXJFSA-N
Standard InCHI:	InChI=1S/C21H18O6/c1-10(7-22)15-3-11-2-13-17(5-16(11)26-15)23-8-14-12-4-19-20(25-9-24-19)6-18(12)27-21(13)14/h2,4-6,14-15,21-22H,1,3,7-9H2/t14-,15+,21-/m0/s1
SMILES:	OCC(=C)[C@H]1Cc2c(O1)cc1c(c2)[C@@H]2Oc3c([C@@H]2CO1)cc1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224756
PubChem CID:	46939793
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[20804165]
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	54400.0	nM	PMID[475822]

☑ 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 NPC240521 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	476
0.1-0.2	1653
0.2-0.3	4308
0.3-0.4	11150
0.4-0.5	7540
0.5-0.6	4475
0.6-0.7	7524
0.7-0.8	4333
0.8-0.85	919
0.85-0.9	286
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC71726
0.9577	High Similarity	NPC205316
0.9441	High Similarity	NPC474749
0.9441	High Similarity	NPC178014
0.9441	High Similarity	NPC11422
0.9441	High Similarity	NPC42716
0.9375	High Similarity	NPC226540
0.9306	High Similarity	NPC180953
0.9262	High Similarity	NPC159922
0.9252	High Similarity	NPC238140
0.9247	High Similarity	NPC301961
0.9247	High Similarity	NPC166584
0.9241	High Similarity	NPC162193
0.9231	High Similarity	NPC472562
0.9231	High Similarity	NPC80326
0.9172	High Similarity	NPC307466
0.9167	High Similarity	NPC474808
0.9161	High Similarity	NPC300798
0.9161	High Similarity	NPC58137
0.9122	High Similarity	NPC472709
0.9122	High Similarity	NPC472710
0.9116	High Similarity	NPC270751
0.9097	High Similarity	NPC174522
0.9091	High Similarity	NPC46591
0.9048	High Similarity	NPC116019
0.9034	High Similarity	NPC47633
0.9034	High Similarity	NPC85264
0.9034	High Similarity	NPC102044
0.9021	High Similarity	NPC9068
0.9021	High Similarity	NPC292487
0.8986	High Similarity	NPC248132
0.8986	High Similarity	NPC130449
0.8973	High Similarity	NPC12641
0.8973	High Similarity	NPC93323
0.8973	High Similarity	NPC280092
0.8973	High Similarity	NPC45257
0.8973	High Similarity	NPC63879
0.8966	High Similarity	NPC311057
0.8958	High Similarity	NPC226547
0.8958	High Similarity	NPC27495
0.8958	High Similarity	NPC56091
0.8951	High Similarity	NPC477938
0.8944	High Similarity	NPC18576
0.8926	High Similarity	NPC55158
0.8926	High Similarity	NPC286235
0.8926	High Similarity	NPC51328
0.8919	High Similarity	NPC101376
0.8912	High Similarity	NPC476301
0.8912	High Similarity	NPC43508
0.8904	High Similarity	NPC12728
0.8904	High Similarity	NPC255566
0.8904	High Similarity	NPC185071
0.8904	High Similarity	NPC298317
0.8897	High Similarity	NPC247291
0.8889	High Similarity	NPC471388
0.8881	High Similarity	NPC197166
0.8881	High Similarity	NPC78047
0.8874	High Similarity	NPC302610
0.8873	High Similarity	NPC31530
0.8873	High Similarity	NPC47181
0.8867	High Similarity	NPC98624
0.8859	High Similarity	NPC175976
0.8851	High Similarity	NPC33832
0.8844	High Similarity	NPC141569
0.8844	High Similarity	NPC217635
0.8844	High Similarity	NPC471667
0.8844	High Similarity	NPC477701
0.8844	High Similarity	NPC239254
0.8844	High Similarity	NPC166884
0.8844	High Similarity	NPC79429
0.8844	High Similarity	NPC172171
0.8836	High Similarity	NPC107161
0.8828	High Similarity	NPC259519
0.8828	High Similarity	NPC177868
0.8819	High Similarity	NPC185908
0.8819	High Similarity	NPC283949
0.8811	High Similarity	NPC148893
0.8811	High Similarity	NPC25333
0.8811	High Similarity	NPC49235
0.8811	High Similarity	NPC189474
0.8811	High Similarity	NPC150534
0.88	High Similarity	NPC95392
0.88	High Similarity	NPC55715
0.88	High Similarity	NPC35877
0.8792	High Similarity	NPC193473
0.8792	High Similarity	NPC21776
0.8792	High Similarity	NPC39657
0.8792	High Similarity	NPC213074
0.8792	High Similarity	NPC15956
0.8792	High Similarity	NPC275284
0.8792	High Similarity	NPC16269
0.8792	High Similarity	NPC31325
0.8792	High Similarity	NPC114505
0.8792	High Similarity	NPC224674
0.8792	High Similarity	NPC227902
0.8784	High Similarity	NPC475868
0.8784	High Similarity	NPC469586
0.8776	High Similarity	NPC81638
0.8776	High Similarity	NPC252169
0.8767	High Similarity	NPC311530
0.8767	High Similarity	NPC471389
0.8767	High Similarity	NPC263261
0.8767	High Similarity	NPC87725
0.8767	High Similarity	NPC471908
0.8767	High Similarity	NPC312199
0.8766	High Similarity	NPC189730
0.8759	High Similarity	NPC6369
0.8759	High Similarity	NPC30951
0.875	High Similarity	NPC173660
0.875	High Similarity	NPC172818
0.875	High Similarity	NPC25695
0.8741	High Similarity	NPC474478
0.8741	High Similarity	NPC90083
0.8741	High Similarity	NPC170779
0.8732	High Similarity	NPC72046
0.8732	High Similarity	NPC65183
0.8732	High Similarity	NPC261812
0.8725	High Similarity	NPC99515
0.8725	High Similarity	NPC190714
0.8716	High Similarity	NPC187774
0.8716	High Similarity	NPC473046
0.8716	High Similarity	NPC179521
0.8716	High Similarity	NPC472712
0.8716	High Similarity	NPC118385
0.8716	High Similarity	NPC472713
0.8707	High Similarity	NPC41782
0.8707	High Similarity	NPC229172
0.8707	High Similarity	NPC253878
0.8707	High Similarity	NPC103637
0.8707	High Similarity	NPC474295
0.8707	High Similarity	NPC246947
0.8707	High Similarity	NPC287124
0.8707	High Similarity	NPC230538
0.8707	High Similarity	NPC36531
0.8701	High Similarity	NPC164152
0.8699	High Similarity	NPC284464
0.8699	High Similarity	NPC309124
0.8699	High Similarity	NPC160283
0.8699	High Similarity	NPC184797
0.8699	High Similarity	NPC254759
0.869	High Similarity	NPC469981
0.869	High Similarity	NPC474039
0.8681	High Similarity	NPC195022
0.8671	High Similarity	NPC266848
0.8671	High Similarity	NPC26394
0.8671	High Similarity	NPC112237
0.8671	High Similarity	NPC196937
0.8671	High Similarity	NPC58585
0.8671	High Similarity	NPC136750
0.8658	High Similarity	NPC277867
0.8658	High Similarity	NPC279298
0.8658	High Similarity	NPC475096
0.8658	High Similarity	NPC161700
0.8658	High Similarity	NPC469557
0.8658	High Similarity	NPC22150
0.8658	High Similarity	NPC181615
0.8658	High Similarity	NPC38041
0.8649	High Similarity	NPC324962
0.8649	High Similarity	NPC477616
0.8649	High Similarity	NPC265154
0.8649	High Similarity	NPC37793
0.8639	High Similarity	NPC471414
0.8639	High Similarity	NPC469661
0.863	High Similarity	NPC236306
0.863	High Similarity	NPC193666
0.863	High Similarity	NPC292882
0.863	High Similarity	NPC25966
0.863	High Similarity	NPC473739
0.863	High Similarity	NPC245207
0.863	High Similarity	NPC123526
0.863	High Similarity	NPC127218
0.863	High Similarity	NPC232164
0.863	High Similarity	NPC113550
0.863	High Similarity	NPC156376
0.863	High Similarity	NPC88640
0.863	High Similarity	NPC70682
0.863	High Similarity	NPC319647
0.863	High Similarity	NPC260741
0.8621	High Similarity	NPC470802
0.8618	High Similarity	NPC473989
0.8611	High Similarity	NPC16485
0.8601	High Similarity	NPC230219
0.8601	High Similarity	NPC259742
0.8601	High Similarity	NPC104077
0.8601	High Similarity	NPC219671
0.8601	High Similarity	NPC7744
0.8601	High Similarity	NPC147616
0.86	High Similarity	NPC212890
0.86	High Similarity	NPC154971
0.86	High Similarity	NPC260397
0.86	High Similarity	NPC317053
0.86	High Similarity	NPC252286
0.86	High Similarity	NPC324492
0.86	High Similarity	NPC125755
0.86	High Similarity	NPC112861
0.8591	High Similarity	NPC168579
0.8591	High Similarity	NPC138227
0.8591	High Similarity	NPC50250
0.8591	High Similarity	NPC25292
0.8591	High Similarity	NPC469313

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 NPC240521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	919
0.2-0.3	2004
0.3-0.4	2759
0.4-0.5	1583
0.5-0.6	865
0.6-0.7	535
0.7-0.8	74
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8408	Intermediate Similarity	NPD4966	Approved
0.8408	Intermediate Similarity	NPD4967	Phase 2
0.8408	Intermediate Similarity	NPD4965	Approved
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD37	Approved
0.8187	Intermediate Similarity	NPD6234	Discontinued
0.8146	Intermediate Similarity	NPD6674	Discontinued
0.8125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1653	Approved
0.8069	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7228	Approved
0.8014	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7975	Intermediate Similarity	NPD7199	Phase 2
0.7959	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1610	Phase 2
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7240	Approved
0.7738	Intermediate Similarity	NPD3818	Discontinued
0.7708	Intermediate Similarity	NPD3705	Approved
0.7708	Intermediate Similarity	NPD1091	Approved
0.7697	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD5844	Phase 1
0.76	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7074	Phase 3
0.7533	Intermediate Similarity	NPD4625	Phase 3
0.7532	Intermediate Similarity	NPD5058	Phase 3
0.7514	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7054	Approved
0.7483	Intermediate Similarity	NPD4749	Approved
0.7457	Intermediate Similarity	NPD6559	Discontinued
0.7452	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7472	Approved
0.7439	Intermediate Similarity	NPD1934	Approved
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.741	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1357	Approved
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7333	Intermediate Similarity	NPD3384	Approved
0.7333	Intermediate Similarity	NPD3383	Approved
0.7333	Intermediate Similarity	NPD3382	Approved
0.7314	Intermediate Similarity	NPD7808	Phase 3
0.7308	Intermediate Similarity	NPD5588	Approved
0.7299	Intermediate Similarity	NPD6797	Phase 2
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7289	Intermediate Similarity	NPD2801	Approved
0.7285	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7262	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7680	Approved
0.7257	Intermediate Similarity	NPD7251	Discontinued
0.7232	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7549	Discontinued
0.7215	Intermediate Similarity	NPD7266	Discontinued
0.7209	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6166	Phase 2
0.7209	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5283	Phase 1
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4536	Approved
0.7134	Intermediate Similarity	NPD4538	Approved
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD2983	Phase 2
0.7117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4380	Phase 2
0.7101	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD5126	Approved
0.7095	Intermediate Similarity	NPD5125	Phase 3
0.7089	Intermediate Similarity	NPD5960	Phase 3
0.7086	Intermediate Similarity	NPD8651	Approved
0.7086	Intermediate Similarity	NPD6696	Suspended
0.7081	Intermediate Similarity	NPD6331	Phase 2
0.7081	Intermediate Similarity	NPD3892	Phase 2
0.7073	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2981	Phase 2
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3817	Phase 2
0.7032	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3751	Discontinued
0.7019	Intermediate Similarity	NPD5177	Phase 3
0.7019	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD5735	Approved
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6005	Phase 3
0.7	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD5763	Approved
0.6994	Remote Similarity	NPD7229	Phase 3
0.6994	Remote Similarity	NPD6232	Discontinued
0.6986	Remote Similarity	NPD6671	Approved
0.6982	Remote Similarity	NPD7819	Suspended
0.6982	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1465	Phase 2
0.6981	Remote Similarity	NPD4108	Discontinued
0.6975	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7473	Discontinued
0.6961	Remote Similarity	NPD4663	Approved
0.6959	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD2970	Approved
0.6954	Remote Similarity	NPD2969	Approved
0.6951	Remote Similarity	NPD1511	Approved
0.6946	Remote Similarity	NPD4005	Discontinued
0.6941	Remote Similarity	NPD5402	Approved
0.6941	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6099	Approved
0.6937	Remote Similarity	NPD6100	Approved
0.6937	Remote Similarity	NPD3454	Phase 3
0.6933	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6841	Approved
0.6923	Remote Similarity	NPD6843	Phase 3
0.6923	Remote Similarity	NPD6842	Approved
0.6918	Remote Similarity	NPD7097	Phase 1
0.6909	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4678	Approved
0.6905	Remote Similarity	NPD4675	Approved
0.6899	Remote Similarity	NPD6355	Discontinued
0.6897	Remote Similarity	NPD3051	Approved
0.6894	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2977	Approved
0.6882	Remote Similarity	NPD2978	Approved
0.6875	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7466	Approved
0.6871	Remote Similarity	NPD4110	Phase 3
0.6867	Remote Similarity	NPD1512	Approved
0.6852	Remote Similarity	NPD1549	Phase 2
0.6852	Remote Similarity	NPD2424	Discontinued
0.6848	Remote Similarity	NPD7212	Phase 2
0.6848	Remote Similarity	NPD7213	Phase 3
0.6842	Remote Similarity	NPD2563	Approved
0.6842	Remote Similarity	NPD2560	Approved
0.6839	Remote Similarity	NPD8127	Discontinued
0.6839	Remote Similarity	NPD1247	Approved
0.6839	Remote Similarity	NPD6959	Discontinued
0.6835	Remote Similarity	NPD4140	Approved
0.6831	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6801	Discontinued
0.6818	Remote Similarity	NPD27	Approved
0.6818	Remote Similarity	NPD2489	Approved
0.681	Remote Similarity	NPD4237	Approved
0.681	Remote Similarity	NPD4236	Phase 3
0.6807	Remote Similarity	NPD7447	Phase 1
0.6805	Remote Similarity	NPD7028	Phase 2
0.68	Remote Similarity	NPD6071	Discontinued
0.6796	Remote Similarity	NPD8313	Approved
0.6796	Remote Similarity	NPD4577	Approved
0.6796	Remote Similarity	NPD4578	Approved
0.6796	Remote Similarity	NPD8312	Approved
0.679	Remote Similarity	NPD3540	Phase 1
0.679	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5929	Approved
0.6778	Remote Similarity	NPD7685	Pre-registration
0.6776	Remote Similarity	NPD422	Phase 1
0.6772	Remote Similarity	NPD6233	Phase 2
0.677	Remote Similarity	NPD7033	Discontinued
0.6768	Remote Similarity	NPD3750	Approved
0.6766	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7411	Suspended
0.6757	Remote Similarity	NPD7157	Approved
0.6746	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7906	Approved
0.6736	Remote Similarity	NPD2684	Approved
0.673	Remote Similarity	NPD2238	Phase 2
0.6728	Remote Similarity	NPD3539	Phase 1
0.6728	Remote Similarity	NPD2161	Phase 2
0.6728	Remote Similarity	NPD2935	Discontinued
0.6727	Remote Similarity	NPD2677	Approved
0.6724	Remote Similarity	NPD919	Approved
0.672	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD968	Approved
0.6712	Remote Similarity	NPD228	Approved
0.6711	Remote Similarity	NPD7340	Approved
0.6711	Remote Similarity	NPD3496	Discontinued
0.6709	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6798	Discontinued

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