NPASS Compound

Structure

NPC474478 OpenBabel07101718332D 23 26 0 0 1 0 0 0 0 0999 V2000 3.5714 -1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.5316 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 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.8271 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 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 22 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 15 2 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	313.791
LogP:	3.022
LogD:	3.395
LogS:	-4.441
# Rotatable Bonds:	3
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.869
Synthetic Accessibility Score:	3.079
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.958
MDCK Permeability:	6.062588727218099e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	92.01083374023438%
Volume Distribution (VD):	0.852
Pgp-substrate:	4.363256931304932%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.263
CYP2D6-substrate:	0.94
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	6.939
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.606
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.522
Carcinogencity:	0.319
Eye Corrosion:	0.003
Eye Irritation:	0.086
Respiratory Toxicity:	0.533

Download Data

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

Natural Product: NPC474478

Natural Product ID:	NPC474478
*Common Name:**	2,3,9-Trimethoxypterocarpan
IUPAC Name:	2,3,9-trimethoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene
Synonyms:	2,3,9-Trimethoxypterocarpan
Standard InCHIKey:	XCRBPIBUMBLGCZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-19-10-4-5-11-13-9-22-14-8-17(21-3)16(20-2)7-12(14)18(13)23-15(11)6-10/h4-8,13,18H,9H2,1-3H3
SMILES:	COC1=CC2=C(C=C1)C3COC4=CC(=C(C=C4C3O2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469708
PubChem CID:	11151159
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
NPO24543	Platymiscium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787450]
NPO24543	Platymiscium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO24543	Platymiscium floribundum	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	9
Others	6

Activity Type	# Activity
Cell Line	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	0.6	ug.mL-1	PMID[449669]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[449669]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	0.6	ug.mL-1	PMID[449669]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.7	ug.mL-1	PMID[449669]
NPT319	Cell Line	B16	Mus musculus	IC50	=	2.9	ug.mL-1	PMID[449669]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	760.0	nM	PMID[449670]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	11360.0	nM	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC50	=	5930.0	nM	PMID[449670]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	13970.0	nM	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	52.61	%	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	46.72	%	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	10.02	%	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	10.93	%	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	37.16	%	PMID[449670]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	42.06	%	PMID[449670]

☑ 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 NPC474478 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	545
0.1-0.2	1737
0.2-0.3	5200
0.3-0.4	13237
0.4-0.5	4403
0.5-0.6	4749
0.6-0.7	7677
0.7-0.8	3969
0.8-0.85	819
0.85-0.9	302
0.9-0.95	57
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9621	High Similarity	NPC27495
0.9542	High Similarity	NPC78047
0.9531	High Similarity	NPC237169
0.9531	High Similarity	NPC470624
0.9528	High Similarity	NPC31707
0.9478	High Similarity	NPC107161
0.9478	High Similarity	NPC80326
0.9403	High Similarity	NPC58137
0.9403	High Similarity	NPC247291
0.9403	High Similarity	NPC300798
0.9398	High Similarity	NPC471388
0.9394	High Similarity	NPC173660
0.937	High Similarity	NPC50683
0.937	High Similarity	NPC112571
0.937	High Similarity	NPC285725
0.9338	High Similarity	NPC45257
0.9338	High Similarity	NPC93323
0.9338	High Similarity	NPC12641
0.9338	High Similarity	NPC280092
0.9333	High Similarity	NPC174522
0.9328	High Similarity	NPC254759
0.9328	High Similarity	NPC160283
0.9328	High Similarity	NPC184797
0.9328	High Similarity	NPC309124
0.9318	High Similarity	NPC195022
0.9265	High Similarity	NPC85264
0.9265	High Similarity	NPC47633
0.9265	High Similarity	NPC102044
0.9259	High Similarity	NPC471389
0.9254	High Similarity	NPC236306
0.9254	High Similarity	NPC232164
0.9254	High Similarity	NPC473739
0.9254	High Similarity	NPC245207
0.9254	High Similarity	NPC127218
0.9254	High Similarity	NPC292882
0.9254	High Similarity	NPC25966
0.9254	High Similarity	NPC319647
0.9225	High Similarity	NPC222127
0.9225	High Similarity	NPC82862
0.9219	High Similarity	NPC9891
0.9219	High Similarity	NPC88297
0.9219	High Similarity	NPC186845
0.9213	High Similarity	NPC294156
0.9213	High Similarity	NPC256015
0.9197	High Similarity	NPC63879
0.9191	High Similarity	NPC472562
0.9179	High Similarity	NPC107551
0.9179	High Similarity	NPC474282
0.9179	High Similarity	NPC276490
0.9179	High Similarity	NPC477938
0.9179	High Similarity	NPC176051
0.9179	High Similarity	NPC326797
0.9179	High Similarity	NPC103976
0.9179	High Similarity	NPC102904
0.9167	High Similarity	NPC263064
0.9147	High Similarity	NPC8050
0.9147	High Similarity	NPC473092
0.9147	High Similarity	NPC98745
0.9147	High Similarity	NPC473093
0.9137	High Similarity	NPC21776
0.9137	High Similarity	NPC16269
0.913	High Similarity	NPC205316
0.9124	High Similarity	NPC477616
0.9118	High Similarity	NPC311530
0.9104	High Similarity	NPC265433
0.9104	High Similarity	NPC248727
0.9104	High Similarity	NPC270456
0.9104	High Similarity	NPC162659
0.9091	High Similarity	NPC475856
0.9077	High Similarity	NPC281864
0.9077	High Similarity	NPC54321
0.9077	High Similarity	NPC328682
0.9055	High Similarity	NPC261661
0.9044	High Similarity	NPC259519
0.903	High Similarity	NPC311430
0.903	High Similarity	NPC112939
0.903	High Similarity	NPC112246
0.903	High Similarity	NPC474206
0.903	High Similarity	NPC470356
0.903	High Similarity	NPC61946
0.903	High Similarity	NPC224941
0.903	High Similarity	NPC94750
0.903	High Similarity	NPC134968
0.903	High Similarity	NPC121812
0.9	High Similarity	NPC202904
0.9	High Similarity	NPC189248
0.9	High Similarity	NPC101376
0.8993	High Similarity	NPC474749
0.8993	High Similarity	NPC307466
0.8993	High Similarity	NPC42716
0.8993	High Similarity	NPC469557
0.8993	High Similarity	NPC11422
0.8993	High Similarity	NPC178014
0.8978	High Similarity	NPC263261
0.8978	High Similarity	NPC87725
0.8976	High Similarity	NPC312713
0.8976	High Similarity	NPC172676
0.8976	High Similarity	NPC57268
0.8976	High Similarity	NPC216929
0.8976	High Similarity	NPC126935
0.8976	High Similarity	NPC65933
0.8971	High Similarity	NPC70682
0.8971	High Similarity	NPC260741
0.8963	High Similarity	NPC16435
0.8963	High Similarity	NPC306441
0.8963	High Similarity	NPC474639
0.8963	High Similarity	NPC230734
0.8963	High Similarity	NPC472334
0.8963	High Similarity	NPC472336
0.8963	High Similarity	NPC227503
0.8955	High Similarity	NPC317380
0.8947	High Similarity	NPC230219
0.8939	High Similarity	NPC192687
0.8939	High Similarity	NPC476399
0.8939	High Similarity	NPC224157
0.8936	High Similarity	NPC71726
0.8936	High Similarity	NPC166584
0.8936	High Similarity	NPC301961
0.8929	High Similarity	NPC162193
0.8921	High Similarity	NPC50250
0.8915	High Similarity	NPC121783
0.8915	High Similarity	NPC34902
0.8915	High Similarity	NPC18449
0.8898	High Similarity	NPC472596
0.8897	High Similarity	NPC211549
0.8889	High Similarity	NPC151224
0.8889	High Similarity	NPC234333
0.8889	High Similarity	NPC472337
0.8889	High Similarity	NPC260898
0.8889	High Similarity	NPC47398
0.8881	High Similarity	NPC136750
0.8881	High Similarity	NPC11060
0.8881	High Similarity	NPC26394
0.8881	High Similarity	NPC158331
0.8881	High Similarity	NPC266848
0.8872	High Similarity	NPC162801
0.8872	High Similarity	NPC141493
0.8872	High Similarity	NPC184928
0.8864	High Similarity	NPC190144
0.8864	High Similarity	NPC474227
0.8857	High Similarity	NPC181615
0.8855	High Similarity	NPC242032
0.8849	High Similarity	NPC258083
0.8849	High Similarity	NPC81638
0.8841	High Similarity	NPC35216
0.8832	High Similarity	NPC292487
0.8828	High Similarity	NPC477886
0.8824	High Similarity	NPC269091
0.8824	High Similarity	NPC286843
0.8824	High Similarity	NPC302701
0.8824	High Similarity	NPC234952
0.8819	High Similarity	NPC160196
0.8815	High Similarity	NPC474600
0.8815	High Similarity	NPC287745
0.8815	High Similarity	NPC16485
0.8815	High Similarity	NPC478085
0.8815	High Similarity	NPC106215
0.8811	High Similarity	NPC238140
0.8806	High Similarity	NPC6451
0.8806	High Similarity	NPC7744
0.8806	High Similarity	NPC127624
0.8806	High Similarity	NPC202762
0.8806	High Similarity	NPC261812
0.8806	High Similarity	NPC204215
0.8806	High Similarity	NPC86655
0.8806	High Similarity	NPC72046
0.8806	High Similarity	NPC65183
0.8806	High Similarity	NPC175067
0.8803	High Similarity	NPC270751
0.8794	High Similarity	NPC226540
0.8794	High Similarity	NPC324492
0.8794	High Similarity	NPC260397
0.8794	High Similarity	NPC317053
0.8788	High Similarity	NPC210674
0.8788	High Similarity	NPC47283
0.8788	High Similarity	NPC39064
0.8786	High Similarity	NPC473108
0.8779	High Similarity	NPC244364
0.8779	High Similarity	NPC206882
0.8777	High Similarity	NPC2613
0.8777	High Similarity	NPC311057
0.8777	High Similarity	NPC204347
0.8777	High Similarity	NPC475891
0.8777	High Similarity	NPC59841
0.876	High Similarity	NPC194626
0.8759	High Similarity	NPC196420
0.875	High Similarity	NPC126409
0.875	High Similarity	NPC234865
0.875	High Similarity	NPC189474
0.875	High Similarity	NPC99572
0.875	High Similarity	NPC473413
0.875	High Similarity	NPC164787
0.8741	High Similarity	NPC85435
0.8741	High Similarity	NPC240521
0.8741	High Similarity	NPC475840
0.8741	High Similarity	NPC229442
0.8741	High Similarity	NPC1474
0.8741	High Similarity	NPC168059
0.874	High Similarity	NPC59561
0.874	High Similarity	NPC308217

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 NPC474478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	931
0.2-0.3	1848
0.3-0.4	2740
0.4-0.5	1609
0.5-0.6	906
0.6-0.7	574
0.7-0.8	97
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD1613	Approved
0.8667	High Similarity	NPD1612	Clinical (unspecified phase)
0.8507	High Similarity	NPD1529	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD3027	Phase 3
0.8433	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8433	Intermediate Similarity	NPD2861	Phase 2
0.8411	Intermediate Similarity	NPD5494	Approved
0.837	Intermediate Similarity	NPD4908	Phase 1
0.8268	Intermediate Similarity	NPD5283	Phase 1
0.8258	Intermediate Similarity	NPD1610	Phase 2
0.8248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD3018	Phase 2
0.806	Intermediate Similarity	NPD2981	Phase 2
0.8	Intermediate Similarity	NPD2982	Phase 2
0.8	Intermediate Similarity	NPD2983	Phase 2
0.7985	Intermediate Similarity	NPD3705	Approved
0.7895	Intermediate Similarity	NPD1934	Approved
0.7868	Intermediate Similarity	NPD4749	Approved
0.7852	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1548	Phase 1
0.7815	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4625	Phase 3
0.7778	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7755	Intermediate Similarity	NPD7466	Approved
0.7748	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD4967	Phase 2
0.7742	Intermediate Similarity	NPD4966	Approved
0.7742	Intermediate Similarity	NPD4965	Approved
0.773	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2801	Approved
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5844	Phase 1
0.7687	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6674	Discontinued
0.7673	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6234	Discontinued
0.7603	Intermediate Similarity	NPD3539	Phase 1
0.7564	Intermediate Similarity	NPD3817	Phase 2
0.7564	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3540	Phase 1
0.7548	Intermediate Similarity	NPD3383	Approved
0.7548	Intermediate Similarity	NPD3384	Approved
0.7548	Intermediate Similarity	NPD3382	Approved
0.7533	Intermediate Similarity	NPD7124	Phase 2
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3882	Suspended
0.7515	Intermediate Similarity	NPD7549	Discontinued
0.7483	Intermediate Similarity	NPD2796	Approved
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5327	Phase 3
0.7463	Intermediate Similarity	NPD6671	Approved
0.7451	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1247	Approved
0.7429	Intermediate Similarity	NPD8651	Approved
0.7423	Intermediate Similarity	NPD7228	Approved
0.7423	Intermediate Similarity	NPD3818	Discontinued
0.7415	Intermediate Similarity	NPD5588	Approved
0.74	Intermediate Similarity	NPD3892	Phase 2
0.74	Intermediate Similarity	NPD6331	Phase 2
0.7386	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4060	Phase 1
0.7358	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7347	Intermediate Similarity	NPD4536	Approved
0.7347	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6111	Discontinued
0.7347	Intermediate Similarity	NPD4538	Approved
0.7346	Intermediate Similarity	NPD3926	Phase 2
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1091	Approved
0.7333	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD5177	Phase 3
0.7333	Intermediate Similarity	NPD1652	Phase 2
0.7333	Intermediate Similarity	NPD7157	Approved
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.7329	Intermediate Similarity	NPD3657	Discovery
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2684	Approved
0.7324	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1375	Discontinued
0.7308	Intermediate Similarity	NPD4678	Approved
0.7308	Intermediate Similarity	NPD4675	Approved
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7285	Intermediate Similarity	NPD4110	Phase 3
0.7285	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD8156	Discontinued
0.726	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3620	Phase 2
0.7255	Intermediate Similarity	NPD7213	Phase 3
0.7255	Intermediate Similarity	NPD1511	Approved
0.7255	Intermediate Similarity	NPD7212	Phase 2
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7246	Intermediate Similarity	NPD7240	Approved
0.7244	Intermediate Similarity	NPD4005	Discontinued
0.7241	Intermediate Similarity	NPD5109	Approved
0.7241	Intermediate Similarity	NPD5111	Phase 2
0.7241	Intermediate Similarity	NPD5110	Phase 2
0.7239	Intermediate Similarity	NPD5535	Approved
0.7239	Intermediate Similarity	NPD7843	Approved
0.723	Intermediate Similarity	NPD2200	Suspended
0.7229	Intermediate Similarity	NPD7472	Approved
0.7219	Intermediate Similarity	NPD4236	Phase 3
0.7219	Intermediate Similarity	NPD4237	Approved
0.7214	Intermediate Similarity	NPD1611	Approved
0.7212	Intermediate Similarity	NPD8251	Approved
0.7212	Intermediate Similarity	NPD8099	Discontinued
0.7212	Intermediate Similarity	NPD8252	Approved
0.7211	Intermediate Similarity	NPD5735	Approved
0.7208	Intermediate Similarity	NPD7447	Phase 1
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD919	Approved
0.7202	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5762	Approved
0.72	Intermediate Similarity	NPD5763	Approved
0.72	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4481	Phase 3
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.7183	Intermediate Similarity	NPD6696	Suspended
0.7181	Intermediate Similarity	NPD5960	Phase 3
0.7181	Intermediate Similarity	NPD3748	Approved
0.7179	Intermediate Similarity	NPD4210	Discontinued
0.7178	Intermediate Similarity	NPD3051	Approved
0.7178	Intermediate Similarity	NPD7229	Phase 3
0.717	Intermediate Similarity	NPD7819	Suspended
0.717	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD228	Approved
0.7161	Intermediate Similarity	NPD1512	Approved
0.716	Intermediate Similarity	NPD5677	Discontinued
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7134	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2969	Approved
0.7134	Intermediate Similarity	NPD2970	Approved
0.7133	Intermediate Similarity	NPD2161	Phase 2
0.7133	Intermediate Similarity	NPD3454	Phase 3
0.7133	Intermediate Similarity	NPD4098	Discontinued
0.7125	Intermediate Similarity	NPD2563	Approved
0.7125	Intermediate Similarity	NPD5402	Approved
0.7125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2560	Approved
0.7124	Intermediate Similarity	NPD2677	Approved
0.7123	Intermediate Similarity	NPD6798	Discontinued
0.7122	Intermediate Similarity	NPD1357	Approved
0.7122	Intermediate Similarity	NPD5585	Approved
0.7121	Intermediate Similarity	NPD290	Approved
0.7115	Intermediate Similarity	NPD5976	Discontinued
0.7113	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7808	Phase 3
0.7097	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD422	Phase 1
0.7089	Intermediate Similarity	NPD4380	Phase 2
0.7086	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6797	Phase 2
0.7081	Intermediate Similarity	NPD6788	Approved
0.7075	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6071	Discontinued
0.7073	Intermediate Similarity	NPD3787	Discontinued
0.7073	Intermediate Similarity	NPD6232	Discontinued
0.7071	Intermediate Similarity	NPD17	Approved
0.7071	Intermediate Similarity	NPD6516	Phase 2
0.7071	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD2922	Phase 1
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1182	Approved
0.7048	Intermediate Similarity	NPD3489	Phase 3
0.7048	Intermediate Similarity	NPD7473	Discontinued
0.7045	Intermediate Similarity	NPD968	Approved
0.7042	Intermediate Similarity	NPD1840	Phase 2
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7041	Intermediate Similarity	NPD7251	Discontinued
0.7039	Intermediate Similarity	NPD2424	Discontinued
0.7039	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4055	Discovery
0.7037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7075	Discontinued
0.7035	Intermediate Similarity	NPD4663	Approved
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.7032	Intermediate Similarity	NPD5297	Approved
0.7032	Intermediate Similarity	NPD6799	Approved
0.7032	Intermediate Similarity	NPD1774	Approved
0.7027	Intermediate Similarity	NPD1558	Phase 1
0.7027	Intermediate Similarity	NPD2238	Phase 2

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