NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.09
Volume:	276.329
LogP:	2.926
LogD:	2.639
LogS:	-4.073
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.911
Synthetic Accessibility Score:	2.588
Fsp3:	0.188
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:	-4.744
MDCK Permeability:	2.085242886096239e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.768

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	97.46418762207031%
Volume Distribution (VD):	0.522
Pgp-substrate:	1.5952566862106323%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.954
CYP2C19-substrate:	0.481
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	9.223
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.816
Rat Oral Acute Toxicity:	0.501
Maximum Recommended Daily Dose:	0.167
Skin Sensitization:	0.294
Carcinogencity:	0.476
Eye Corrosion:	0.003
Eye Irritation:	0.114
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC202981

Natural Product ID:	NPC202981
*Common Name:**	(3S)-Sativanone
IUPAC Name:	(3S)-7-hydroxy-3-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	(3S)-Sativanone
Standard InCHIKey:	INYISIYHXQDCPK-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C16H14O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-8,14,17H,9H2,1H3/t14-/m1/s1
SMILES:	COc1ccc(cc1)[C@H]1COc2c(C1=O)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087010
PubChem CID:	46881075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	1.1	uM	PMID[505048]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.7	uM	PMID[505048]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[505048]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	9.2	uM	PMID[505048]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	2.0	uM	PMID[505048]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	8.6	uM	PMID[505048]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	2.7	uM	PMID[505048]

☑ 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 NPC202981 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	355
0.1-0.2	1503
0.2-0.3	3673
0.3-0.4	9336
0.4-0.5	9023
0.5-0.6	3498
0.6-0.7	5412
0.7-0.8	5458
0.8-0.85	2397
0.85-0.9	1282
0.9-0.95	701
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC184649
0.9855	High Similarity	NPC303185
0.9784	High Similarity	NPC299011
0.9783	High Similarity	NPC113770
0.9779	High Similarity	NPC261234
0.9779	High Similarity	NPC316480
0.9712	High Similarity	NPC311144
0.9712	High Similarity	NPC271288
0.9708	High Similarity	NPC129853
0.9708	High Similarity	NPC76445
0.9708	High Similarity	NPC284550
0.9706	High Similarity	NPC280284
0.9706	High Similarity	NPC188947
0.9706	High Similarity	NPC99333
0.9706	High Similarity	NPC118813
0.9645	High Similarity	NPC39195
0.9643	High Similarity	NPC477955
0.9638	High Similarity	NPC3188
0.9635	High Similarity	NPC222342
0.9635	High Similarity	NPC20709
0.9635	High Similarity	NPC225153
0.9635	High Similarity	NPC265871
0.9635	High Similarity	NPC310135
0.9635	High Similarity	NPC274784
0.9635	High Similarity	NPC150648
0.9635	High Similarity	NPC329203
0.9632	High Similarity	NPC275055
0.9632	High Similarity	NPC290291
0.9574	High Similarity	NPC308200
0.9571	High Similarity	NPC473013
0.9571	High Similarity	NPC473015
0.9565	High Similarity	NPC110228
0.9565	High Similarity	NPC188243
0.9565	High Similarity	NPC6407
0.9562	High Similarity	NPC329225
0.9562	High Similarity	NPC124269
0.9562	High Similarity	NPC472460
0.9562	High Similarity	NPC147686
0.9507	High Similarity	NPC145467
0.95	High Similarity	NPC310130
0.95	High Similarity	NPC150408
0.95	High Similarity	NPC169591
0.95	High Similarity	NPC18585
0.95	High Similarity	NPC166138
0.95	High Similarity	NPC106985
0.95	High Similarity	NPC223812
0.95	High Similarity	NPC91560
0.95	High Similarity	NPC143896
0.95	High Similarity	NPC107177
0.95	High Similarity	NPC75049
0.95	High Similarity	NPC164980
0.95	High Similarity	NPC125894
0.95	High Similarity	NPC149026
0.95	High Similarity	NPC221432
0.95	High Similarity	NPC68104
0.95	High Similarity	NPC77794
0.95	High Similarity	NPC39329
0.95	High Similarity	NPC278249
0.95	High Similarity	NPC85162
0.95	High Similarity	NPC81697
0.95	High Similarity	NPC257097
0.95	High Similarity	NPC175504
0.9496	High Similarity	NPC312391
0.9496	High Similarity	NPC213322
0.9496	High Similarity	NPC4743
0.9496	High Similarity	NPC324386
0.9493	High Similarity	NPC140890
0.9489	High Similarity	NPC303644
0.9489	High Similarity	NPC116632
0.9489	High Similarity	NPC266597
0.9489	High Similarity	NPC296490
0.9489	High Similarity	NPC295261
0.9489	High Similarity	NPC188879
0.9489	High Similarity	NPC84585
0.9489	High Similarity	NPC107586
0.9489	High Similarity	NPC32441
0.9489	High Similarity	NPC209560
0.9489	High Similarity	NPC162680
0.9489	High Similarity	NPC294409
0.9489	High Similarity	NPC243083
0.9489	High Similarity	NPC181124
0.9489	High Similarity	NPC228661
0.9489	High Similarity	NPC476480
0.9489	High Similarity	NPC13768
0.9489	High Similarity	NPC12296
0.9489	High Similarity	NPC79943
0.9489	High Similarity	NPC287246
0.9489	High Similarity	NPC250266
0.9489	High Similarity	NPC7013
0.9485	High Similarity	NPC9985
0.9485	High Similarity	NPC239495
0.9441	High Similarity	NPC471114
0.9441	High Similarity	NPC473016
0.9437	High Similarity	NPC300988
0.9437	High Similarity	NPC10990
0.9433	High Similarity	NPC235217
0.9433	High Similarity	NPC131568
0.9433	High Similarity	NPC209040
0.9433	High Similarity	NPC131579
0.9433	High Similarity	NPC473014
0.9433	High Similarity	NPC197252
0.9433	High Similarity	NPC236766
0.9429	High Similarity	NPC148757
0.9429	High Similarity	NPC76372
0.9429	High Similarity	NPC10937
0.9429	High Similarity	NPC32739
0.9429	High Similarity	NPC73028
0.9429	High Similarity	NPC66515
0.9429	High Similarity	NPC166482
0.9429	High Similarity	NPC107572
0.9429	High Similarity	NPC324134
0.9429	High Similarity	NPC161506
0.9429	High Similarity	NPC324436
0.9429	High Similarity	NPC310340
0.9429	High Similarity	NPC37496
0.9429	High Similarity	NPC76338
0.9429	High Similarity	NPC194432
0.9429	High Similarity	NPC166934
0.9429	High Similarity	NPC220998
0.9429	High Similarity	NPC227579
0.9429	High Similarity	NPC228504
0.9429	High Similarity	NPC78
0.9429	High Similarity	NPC167624
0.9429	High Similarity	NPC223500
0.9429	High Similarity	NPC328164
0.9429	High Similarity	NPC177354
0.9429	High Similarity	NPC64915
0.9429	High Similarity	NPC265040
0.9429	High Similarity	NPC40833
0.9429	High Similarity	NPC125855
0.9429	High Similarity	NPC182852
0.9429	High Similarity	NPC296917
0.9429	High Similarity	NPC1089
0.9429	High Similarity	NPC144499
0.9429	High Similarity	NPC306829
0.9424	High Similarity	NPC69769
0.942	High Similarity	NPC279668
0.942	High Similarity	NPC309154
0.942	High Similarity	NPC90665
0.942	High Similarity	NPC278323
0.942	High Similarity	NPC12175
0.942	High Similarity	NPC55162
0.9416	High Similarity	NPC29353
0.9416	High Similarity	NPC124784
0.9416	High Similarity	NPC127447
0.9416	High Similarity	NPC473887
0.9416	High Similarity	NPC231772
0.9416	High Similarity	NPC194281
0.9416	High Similarity	NPC234133
0.9416	High Similarity	NPC240593
0.9416	High Similarity	NPC213603
0.9416	High Similarity	NPC47815
0.9375	High Similarity	NPC267117
0.9375	High Similarity	NPC29777
0.9375	High Similarity	NPC471115
0.9366	High Similarity	NPC196114
0.9366	High Similarity	NPC285630
0.9366	High Similarity	NPC472629
0.9366	High Similarity	NPC127059
0.9362	High Similarity	NPC185276
0.9362	High Similarity	NPC214166
0.9362	High Similarity	NPC316816
0.9362	High Similarity	NPC478086
0.9357	High Similarity	NPC96408
0.9357	High Similarity	NPC248372
0.9357	High Similarity	NPC156190
0.9357	High Similarity	NPC17170
0.9357	High Similarity	NPC279650
0.9357	High Similarity	NPC258630
0.9357	High Similarity	NPC110969
0.9357	High Similarity	NPC110038
0.9357	High Similarity	NPC166689
0.9357	High Similarity	NPC282300
0.9353	High Similarity	NPC18260
0.9353	High Similarity	NPC78913
0.9353	High Similarity	NPC295384
0.9343	High Similarity	NPC234560
0.9343	High Similarity	NPC39426
0.9315	High Similarity	NPC469550
0.931	High Similarity	NPC471229
0.931	High Similarity	NPC178484
0.9306	High Similarity	NPC277032
0.9306	High Similarity	NPC105512
0.9301	High Similarity	NPC24673
0.9301	High Similarity	NPC97716
0.9301	High Similarity	NPC201731
0.9301	High Similarity	NPC237635
0.9301	High Similarity	NPC104406
0.9301	High Similarity	NPC110303
0.9301	High Similarity	NPC296998
0.9301	High Similarity	NPC23728
0.9301	High Similarity	NPC79469
0.9301	High Similarity	NPC473077
0.9296	High Similarity	NPC230943
0.9296	High Similarity	NPC87486
0.9296	High Similarity	NPC124780
0.9296	High Similarity	NPC469764
0.9296	High Similarity	NPC234629
0.9296	High Similarity	NPC470890
0.9296	High Similarity	NPC311741

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 NPC202981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	941
0.2-0.3	1467
0.3-0.4	2496
0.4-0.5	1970
0.5-0.6	1199
0.6-0.7	525
0.7-0.8	146
0.8-0.85	51
0.85-0.9	21
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9562	High Similarity	NPD1549	Phase 2
0.9489	High Similarity	NPD1552	Clinical (unspecified phase)
0.9489	High Similarity	NPD1550	Clinical (unspecified phase)
0.9343	High Similarity	NPD1510	Phase 2
0.9191	High Similarity	NPD1240	Approved
0.9161	High Similarity	NPD4378	Clinical (unspecified phase)
0.9137	High Similarity	NPD2796	Approved
0.9122	High Similarity	NPD8443	Clinical (unspecified phase)
0.9058	High Similarity	NPD1607	Approved
0.8986	High Similarity	NPD1934	Approved
0.8926	High Similarity	NPD7819	Suspended
0.8926	High Similarity	NPD2393	Clinical (unspecified phase)
0.8919	High Similarity	NPD7411	Suspended
0.8897	High Similarity	NPD7410	Clinical (unspecified phase)
0.8874	High Similarity	NPD7075	Discontinued
0.8851	High Similarity	NPD4380	Phase 2
0.88	High Similarity	NPD7096	Clinical (unspecified phase)
0.875	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD3750	Approved
0.8699	High Similarity	NPD6799	Approved
0.8699	High Similarity	NPD1511	Approved
0.8654	High Similarity	NPD7852	Clinical (unspecified phase)
0.8627	High Similarity	NPD3749	Approved
0.8611	High Similarity	NPD970	Clinical (unspecified phase)
0.8601	High Similarity	NPD1551	Phase 2
0.86	High Similarity	NPD6599	Discontinued
0.8581	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD7768	Phase 2
0.8562	High Similarity	NPD3882	Suspended
0.8553	High Similarity	NPD2801	Approved
0.8487	Intermediate Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD6959	Discontinued
0.8425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD2800	Approved
0.8418	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6166	Phase 2
0.8414	Intermediate Similarity	NPD2344	Approved
0.8403	Intermediate Similarity	NPD3748	Approved
0.8397	Intermediate Similarity	NPD5494	Approved
0.8382	Intermediate Similarity	NPD1610	Phase 2
0.8369	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD4908	Phase 1
0.8276	Intermediate Similarity	NPD2799	Discontinued
0.8261	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3817	Phase 2
0.8248	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD6099	Approved
0.8219	Intermediate Similarity	NPD6100	Approved
0.821	Intermediate Similarity	NPD7074	Phase 3
0.8205	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD3818	Discontinued
0.8188	Intermediate Similarity	NPD2309	Approved
0.8176	Intermediate Similarity	NPD1243	Approved
0.8171	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD920	Approved
0.8148	Intermediate Similarity	NPD7054	Approved
0.8146	Intermediate Similarity	NPD5401	Approved
0.8143	Intermediate Similarity	NPD1203	Approved
0.8138	Intermediate Similarity	NPD6651	Approved
0.8133	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4628	Phase 3
0.8098	Intermediate Similarity	NPD7472	Approved
0.8095	Intermediate Similarity	NPD2935	Discontinued
0.8085	Intermediate Similarity	NPD2798	Approved
0.8049	Intermediate Similarity	NPD6797	Phase 2
0.8049	Intermediate Similarity	NPD5953	Discontinued
0.8027	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2532	Approved
0.8026	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2534	Approved
0.8026	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7986	Intermediate Similarity	NPD3268	Approved
0.7986	Intermediate Similarity	NPD2313	Discontinued
0.7972	Intermediate Similarity	NPD6832	Phase 2
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7952	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD6232	Discontinued
0.7935	Intermediate Similarity	NPD3226	Approved
0.7929	Intermediate Similarity	NPD9717	Approved
0.7927	Intermediate Similarity	NPD7286	Phase 2
0.7927	Intermediate Similarity	NPD5844	Phase 1
0.7919	Intermediate Similarity	NPD2346	Discontinued
0.7911	Intermediate Similarity	NPD5402	Approved
0.7887	Intermediate Similarity	NPD2797	Approved
0.7848	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4363	Phase 3
0.7803	Intermediate Similarity	NPD4360	Phase 2
0.7801	Intermediate Similarity	NPD1608	Approved
0.7792	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7785	Intermediate Similarity	NPD7033	Discontinued
0.7785	Intermediate Similarity	NPD4308	Phase 3
0.7764	Intermediate Similarity	NPD919	Approved
0.7762	Intermediate Similarity	NPD3266	Approved
0.7762	Intermediate Similarity	NPD3267	Approved
0.773	Intermediate Similarity	NPD422	Phase 1
0.7725	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1933	Approved
0.7698	Intermediate Similarity	NPD9545	Approved
0.7688	Intermediate Similarity	NPD4288	Approved
0.7676	Intermediate Similarity	NPD3972	Approved
0.7669	Intermediate Similarity	NPD1247	Approved
0.7657	Intermediate Similarity	NPD4361	Phase 2
0.7657	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1613	Approved
0.7622	Intermediate Similarity	NPD4749	Approved
0.7619	Intermediate Similarity	NPD3764	Approved
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.761	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7458	Discontinued
0.7595	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1241	Discontinued
0.7589	Intermediate Similarity	NPD17	Approved
0.7584	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD230	Phase 1
0.7584	Intermediate Similarity	NPD5124	Phase 1
0.7582	Intermediate Similarity	NPD2654	Approved
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2296	Approved
0.7572	Intermediate Similarity	NPD4287	Approved
0.7569	Intermediate Similarity	NPD1876	Approved
0.7569	Intermediate Similarity	NPD3225	Approved
0.7566	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD9493	Approved
0.7551	Intermediate Similarity	NPD4625	Phase 3
0.7545	Intermediate Similarity	NPD3751	Discontinued
0.7534	Intermediate Similarity	NPD2861	Phase 2
0.7534	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1470	Approved
0.7517	Intermediate Similarity	NPD4307	Phase 2
0.7515	Intermediate Similarity	NPD5711	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1201	Approved
0.7471	Intermediate Similarity	NPD6104	Discontinued
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7467	Intermediate Similarity	NPD447	Suspended
0.7466	Intermediate Similarity	NPD1019	Discontinued
0.7456	Intermediate Similarity	NPD1729	Discontinued
0.7455	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD7577	Discontinued
0.7451	Intermediate Similarity	NPD1471	Phase 3
0.7434	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7003	Approved
0.7416	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7229	Phase 3
0.7397	Intermediate Similarity	NPD1164	Approved
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD1296	Phase 2
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6844	Discontinued
0.7346	Intermediate Similarity	NPD6280	Approved
0.7346	Intermediate Similarity	NPD6279	Approved
0.7321	Intermediate Similarity	NPD2403	Approved
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD5760	Phase 2
0.7301	Intermediate Similarity	NPD5761	Phase 2
0.7296	Intermediate Similarity	NPD6273	Approved
0.7285	Intermediate Similarity	NPD3142	Approved
0.7285	Intermediate Similarity	NPD3140	Approved
0.7284	Intermediate Similarity	NPD5890	Approved
0.7284	Intermediate Similarity	NPD5889	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7261	Intermediate Similarity	NPD2354	Approved
0.7257	Intermediate Similarity	NPD8434	Phase 2
0.7243	Intermediate Similarity	NPD7584	Approved
0.7235	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7447	Phase 1
0.7233	Intermediate Similarity	NPD4661	Approved
0.7233	Intermediate Similarity	NPD4662	Approved
0.7219	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1894	Discontinued
0.7202	Intermediate Similarity	NPD6808	Phase 2
0.72	Intermediate Similarity	NPD3027	Phase 3
0.7192	Intermediate Similarity	NPD1481	Phase 2
0.7181	Intermediate Similarity	NPD9494	Approved
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.717	Intermediate Similarity	NPD7213	Phase 3

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