NPASS Compound

Structure

CID311144 OpenBabel06191716122D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 23 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 12 11 1 6 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	3.012
LogD:	2.78
LogS:	-3.964
# Rotatable Bonds:	3
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.905
Synthetic Accessibility Score:	2.945
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.812
MDCK Permeability:	1.8528016880736686e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	98.57630920410156%
Volume Distribution (VD):	0.571
Pgp-substrate:	2.376357078552246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.797
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.753
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.495

ADMET: Excretion

Clearance (CL):	11.115
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.663
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.593
Carcinogencity:	0.162
Eye Corrosion:	0.003
Eye Irritation:	0.408
Respiratory Toxicity:	0.384

Download Data

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

Natural Product: NPC311144

Natural Product ID:	NPC311144
*Common Name:**	Cajanol
IUPAC Name:	(3S)-5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
Synonyms:	Cajanol
Standard InCHIKey:	RYYWWFXWFMYKJM-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-21-10-6-13(19)16-15(7-10)23-8-12(17(16)20)11-4-3-9(18)5-14(11)22-2/h3-7,12,18-19H,8H2,1-2H3/t12-/m1/s1
SMILES:	COc1cc(c2c(c1)OC[C@H](c1ccc(cc1OC)O)C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689287
PubChem CID:	53321436
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids

*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
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21265557]
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	whole plant	Dschang (west region of Cameroon)	2007-SEP	PMID[21265557]
NPO21353	Crotalaria lachnophora	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	9.3	mm	PMID[546988]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	7.3	mm	PMID[546988]

☑ 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 NPC311144 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	362
0.1-0.2	1500
0.2-0.3	3647
0.3-0.4	9085
0.4-0.5	9346
0.5-0.6	3513
0.6-0.7	5256
0.7-0.8	5415
0.8-0.85	2441
0.85-0.9	1488
0.9-0.95	602
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC113770
0.9928	High Similarity	NPC299011
0.9857	High Similarity	NPC308200
0.9856	High Similarity	NPC303185
0.9856	High Similarity	NPC184649
0.9787	High Similarity	NPC39195
0.9787	High Similarity	NPC145467
0.9718	High Similarity	NPC471114
0.9714	High Similarity	NPC271288
0.9712	High Similarity	NPC202981
0.971	High Similarity	NPC129853
0.971	High Similarity	NPC76445
0.971	High Similarity	NPC284550
0.965	High Similarity	NPC471115
0.965	High Similarity	NPC29777
0.9638	High Similarity	NPC316480
0.9568	High Similarity	NPC110228
0.9568	High Similarity	NPC188243
0.9568	High Similarity	NPC6407
0.9565	High Similarity	NPC118813
0.9507	High Similarity	NPC472629
0.9507	High Similarity	NPC477955
0.9504	High Similarity	NPC223812
0.9504	High Similarity	NPC85162
0.9504	High Similarity	NPC278249
0.9504	High Similarity	NPC107177
0.9504	High Similarity	NPC81697
0.9504	High Similarity	NPC77794
0.9504	High Similarity	NPC125894
0.9496	High Similarity	NPC20709
0.9496	High Similarity	NPC140890
0.9496	High Similarity	NPC274784
0.9496	High Similarity	NPC261234
0.9496	High Similarity	NPC265871
0.9496	High Similarity	NPC222342
0.9496	High Similarity	NPC225153
0.9496	High Similarity	NPC150648
0.9496	High Similarity	NPC329203
0.9496	High Similarity	NPC310135
0.9448	High Similarity	NPC471229
0.9444	High Similarity	NPC277032
0.9444	High Similarity	NPC473016
0.9441	High Similarity	NPC10990
0.9441	High Similarity	NPC300988
0.9437	High Similarity	NPC235217
0.9437	High Similarity	NPC131568
0.9437	High Similarity	NPC473013
0.9437	High Similarity	NPC473015
0.9437	High Similarity	NPC87486
0.9437	High Similarity	NPC131579
0.9437	High Similarity	NPC470890
0.9437	High Similarity	NPC124780
0.9437	High Similarity	NPC473014
0.9433	High Similarity	NPC166482
0.9433	High Similarity	NPC76338
0.9433	High Similarity	NPC220998
0.9433	High Similarity	NPC228504
0.9433	High Similarity	NPC227579
0.9433	High Similarity	NPC10937
0.9433	High Similarity	NPC78
0.9433	High Similarity	NPC76372
0.9433	High Similarity	NPC223500
0.9433	High Similarity	NPC328164
0.9433	High Similarity	NPC177354
0.9433	High Similarity	NPC64915
0.9433	High Similarity	NPC265040
0.9433	High Similarity	NPC182852
0.9433	High Similarity	NPC40833
0.9433	High Similarity	NPC125855
0.9433	High Similarity	NPC296917
0.9433	High Similarity	NPC1089
0.9433	High Similarity	NPC306829
0.9433	High Similarity	NPC148757
0.9433	High Similarity	NPC73028
0.9433	High Similarity	NPC66515
0.9433	High Similarity	NPC32739
0.9433	High Similarity	NPC107572
0.9433	High Similarity	NPC166934
0.9433	High Similarity	NPC324134
0.9433	High Similarity	NPC167624
0.9433	High Similarity	NPC194432
0.9433	High Similarity	NPC324436
0.9433	High Similarity	NPC37496
0.9433	High Similarity	NPC161506
0.9424	High Similarity	NPC188947
0.9424	High Similarity	NPC280284
0.9424	High Similarity	NPC124269
0.9424	High Similarity	NPC99333
0.9388	High Similarity	NPC255807
0.9388	High Similarity	NPC31018
0.9384	High Similarity	NPC474843
0.9384	High Similarity	NPC210597
0.9379	High Similarity	NPC267117
0.9371	High Similarity	NPC127059
0.9371	High Similarity	NPC24136
0.9371	High Similarity	NPC187282
0.9371	High Similarity	NPC290133
0.9371	High Similarity	NPC285630
0.9366	High Similarity	NPC185276
0.9366	High Similarity	NPC214166
0.9366	High Similarity	NPC18585
0.9366	High Similarity	NPC91560
0.9366	High Similarity	NPC75049
0.9366	High Similarity	NPC149026
0.9366	High Similarity	NPC150408
0.9366	High Similarity	NPC143896
0.9366	High Similarity	NPC478086
0.9366	High Similarity	NPC221432
0.9366	High Similarity	NPC316816
0.9366	High Similarity	NPC164980
0.9366	High Similarity	NPC169591
0.9366	High Similarity	NPC175504
0.9366	High Similarity	NPC257097
0.9366	High Similarity	NPC106985
0.9366	High Similarity	NPC310130
0.9366	High Similarity	NPC39329
0.9366	High Similarity	NPC68104
0.9366	High Similarity	NPC166138
0.9362	High Similarity	NPC312391
0.9362	High Similarity	NPC110038
0.9362	High Similarity	NPC166689
0.9362	High Similarity	NPC282300
0.9362	High Similarity	NPC3188
0.9362	High Similarity	NPC324386
0.9362	High Similarity	NPC96408
0.9362	High Similarity	NPC213322
0.9362	High Similarity	NPC248372
0.9362	High Similarity	NPC4743
0.9362	High Similarity	NPC258630
0.9362	High Similarity	NPC156190
0.9362	High Similarity	NPC279650
0.9362	High Similarity	NPC17170
0.9353	High Similarity	NPC275055
0.9353	High Similarity	NPC295261
0.9353	High Similarity	NPC13768
0.9353	High Similarity	NPC287246
0.9353	High Similarity	NPC12296
0.9353	High Similarity	NPC107586
0.9353	High Similarity	NPC32441
0.9353	High Similarity	NPC243083
0.9353	High Similarity	NPC79943
0.9353	High Similarity	NPC290291
0.9353	High Similarity	NPC188879
0.9353	High Similarity	NPC296490
0.9324	High Similarity	NPC61112
0.9324	High Similarity	NPC198489
0.932	High Similarity	NPC213608
0.932	High Similarity	NPC1477
0.932	High Similarity	NPC100134
0.932	High Similarity	NPC209760
0.9315	High Similarity	NPC178484
0.931	High Similarity	NPC317492
0.931	High Similarity	NPC266499
0.931	High Similarity	NPC470461
0.9306	High Similarity	NPC296998
0.9306	High Similarity	NPC472918
0.9306	High Similarity	NPC473077
0.9301	High Similarity	NPC236766
0.9301	High Similarity	NPC234629
0.9301	High Similarity	NPC311741
0.9301	High Similarity	NPC273538
0.9301	High Similarity	NPC224714
0.9301	High Similarity	NPC209040
0.9301	High Similarity	NPC216538
0.9301	High Similarity	NPC197252
0.9301	High Similarity	NPC326500
0.9296	High Similarity	NPC310340
0.9296	High Similarity	NPC144499
0.9291	High Similarity	NPC69769
0.9291	High Similarity	NPC159275
0.9291	High Similarity	NPC241100
0.9291	High Similarity	NPC265178
0.9291	High Similarity	NPC182421
0.9286	High Similarity	NPC329225
0.9286	High Similarity	NPC12175
0.9286	High Similarity	NPC55162
0.9286	High Similarity	NPC278323
0.9286	High Similarity	NPC472460
0.9286	High Similarity	NPC309154
0.9286	High Similarity	NPC90665
0.9286	High Similarity	NPC279668
0.9286	High Similarity	NPC147686
0.9281	High Similarity	NPC127447
0.9281	High Similarity	NPC234133
0.9281	High Similarity	NPC29353
0.9281	High Similarity	NPC124784
0.9281	High Similarity	NPC47815
0.9281	High Similarity	NPC13408
0.9281	High Similarity	NPC231772
0.9281	High Similarity	NPC194281
0.9281	High Similarity	NPC473887
0.9281	High Similarity	NPC240593
0.9281	High Similarity	NPC187826
0.9281	High Similarity	NPC213603
0.9275	High Similarity	NPC236974
0.9275	High Similarity	NPC144027
0.9262	High Similarity	NPC271741
0.9262	High Similarity	NPC287789
0.9262	High Similarity	NPC181960
0.9262	High Similarity	NPC129684

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 NPC311144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	925
0.2-0.3	1512
0.3-0.4	2519
0.4-0.5	1944
0.5-0.6	1176
0.6-0.7	511
0.7-0.8	157
0.8-0.85	39
0.85-0.9	25
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9353	High Similarity	NPD1552	Clinical (unspecified phase)
0.9353	High Similarity	NPD1550	Clinical (unspecified phase)
0.9301	High Similarity	NPD4378	Clinical (unspecified phase)
0.9286	High Similarity	NPD1549	Phase 2
0.9128	High Similarity	NPD8443	Clinical (unspecified phase)
0.9071	High Similarity	NPD1510	Phase 2
0.906	High Similarity	NPD2393	Clinical (unspecified phase)
0.9007	High Similarity	NPD2796	Approved
0.8993	High Similarity	NPD1934	Approved
0.8921	High Similarity	NPD1240	Approved
0.8859	High Similarity	NPD4380	Phase 2
0.8808	High Similarity	NPD2801	Approved
0.8808	High Similarity	NPD7819	Suspended
0.88	High Similarity	NPD7411	Suspended
0.8794	High Similarity	NPD1607	Approved
0.8776	High Similarity	NPD7410	Clinical (unspecified phase)
0.8758	High Similarity	NPD7075	Discontinued
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.8707	High Similarity	NPD1511	Approved
0.8684	High Similarity	NPD7096	Clinical (unspecified phase)
0.8591	High Similarity	NPD1512	Approved
0.859	High Similarity	NPD6959	Discontinued
0.8581	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2800	Approved
0.8544	High Similarity	NPD6166	Phase 2
0.8544	High Similarity	NPD6167	Clinical (unspecified phase)
0.8544	High Similarity	NPD7852	Clinical (unspecified phase)
0.8544	High Similarity	NPD6168	Clinical (unspecified phase)
0.8526	High Similarity	NPD5494	Approved
0.8516	High Similarity	NPD3749	Approved
0.8503	High Similarity	NPD3750	Approved
0.8493	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8452	Intermediate Similarity	NPD7768	Phase 2
0.8387	Intermediate Similarity	NPD3817	Phase 2
0.8385	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6801	Discontinued
0.8369	Intermediate Similarity	NPD4908	Phase 1
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8311	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD2344	Approved
0.8288	Intermediate Similarity	NPD2799	Discontinued
0.8278	Intermediate Similarity	NPD2534	Approved
0.8278	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD2533	Approved
0.8272	Intermediate Similarity	NPD7054	Approved
0.8261	Intermediate Similarity	NPD1610	Phase 2
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8252	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD6100	Approved
0.8231	Intermediate Similarity	NPD6099	Approved
0.8221	Intermediate Similarity	NPD7472	Approved
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6797	Phase 2
0.817	Intermediate Similarity	NPD920	Approved
0.8163	Intermediate Similarity	NPD3748	Approved
0.8151	Intermediate Similarity	NPD6651	Approved
0.8133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7251	Discontinued
0.8108	Intermediate Similarity	NPD2935	Discontinued
0.8079	Intermediate Similarity	NPD2309	Approved
0.8072	Intermediate Similarity	NPD7808	Phase 3
0.8072	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5953	Discontinued
0.8052	Intermediate Similarity	NPD5403	Approved
0.8049	Intermediate Similarity	NPD7286	Phase 2
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5402	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD3268	Approved
0.7972	Intermediate Similarity	NPD2798	Approved
0.7949	Intermediate Similarity	NPD3226	Approved
0.7947	Intermediate Similarity	NPD1243	Approved
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7933	Intermediate Similarity	NPD2346	Discontinued
0.7922	Intermediate Similarity	NPD5401	Approved
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4363	Phase 3
0.7919	Intermediate Similarity	NPD4360	Phase 2
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2797	Approved
0.7902	Intermediate Similarity	NPD1203	Approved
0.7895	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD943	Approved
0.7862	Intermediate Similarity	NPD6832	Phase 2
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7848	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7806	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.78	Intermediate Similarity	NPD7033	Discontinued
0.7744	Intermediate Similarity	NPD5711	Approved
0.7744	Intermediate Similarity	NPD5710	Approved
0.7742	Intermediate Similarity	NPD7390	Discontinued
0.7692	Intermediate Similarity	NPD1608	Approved
0.7692	Intermediate Similarity	NPD9717	Approved
0.7683	Intermediate Similarity	NPD1247	Approved
0.7671	Intermediate Similarity	NPD2861	Phase 2
0.767	Intermediate Similarity	NPD4361	Phase 2
0.767	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7651	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1613	Approved
0.7639	Intermediate Similarity	NPD4749	Approved
0.7636	Intermediate Similarity	NPD7229	Phase 3
0.7622	Intermediate Similarity	NPD422	Phase 1
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5124	Phase 1
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD230	Phase 1
0.76	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7582	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3972	Approved
0.7568	Intermediate Similarity	NPD4625	Phase 3
0.7566	Intermediate Similarity	NPD4308	Phase 3
0.7561	Intermediate Similarity	NPD919	Approved
0.756	Intermediate Similarity	NPD3751	Discontinued
0.7551	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2403	Approved
0.753	Intermediate Similarity	NPD3787	Discontinued
0.7517	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD4287	Approved
0.7485	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD2296	Approved
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD1933	Approved
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD6844	Discontinued
0.7466	Intermediate Similarity	NPD3225	Approved
0.7465	Intermediate Similarity	NPD9545	Approved
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5761	Phase 2
0.7423	Intermediate Similarity	NPD5760	Phase 2
0.7415	Intermediate Similarity	NPD1470	Approved
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7384	Intermediate Similarity	NPD6104	Discontinued
0.7381	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1201	Approved
0.7371	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7362	Intermediate Similarity	NPD37	Approved
0.7362	Intermediate Similarity	NPD7577	Discontinued
0.7362	Intermediate Similarity	NPD6280	Approved
0.7362	Intermediate Similarity	NPD6279	Approved
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD6234	Discontinued
0.7347	Intermediate Similarity	NPD1876	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3027	Phase 3
0.7333	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD4965	Approved
0.7325	Intermediate Similarity	NPD7003	Approved
0.7324	Intermediate Similarity	NPD9493	Approved
0.7308	Intermediate Similarity	NPD2424	Discontinued
0.7303	Intermediate Similarity	NPD4307	Phase 2
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7285	Intermediate Similarity	NPD411	Approved
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.7258	Intermediate Similarity	NPD7584	Approved
0.7255	Intermediate Similarity	NPD4618	Approved
0.7255	Intermediate Similarity	NPD4622	Approved
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7447	Phase 1
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD6808	Phase 2
0.7216	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6780	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