NPASS Compound

Structure

CID12070 OpenBabel06191715342D 29 31 0 0 0 0 0 0 0 0999 V2000 0.3893 -4.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 -5.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8409 -4.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5037 -3.1481 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 -1.2838 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7865 -3.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0249 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6559 -2.3827 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -0.5767 -4.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7103 -3.7568 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 0.8660 -1.5000 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 1.7321 -0.0000 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 -2.5981 -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 -0.8660 -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 -1.7321 -2.0000 0.0000 C 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 -1.7321 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 25 1 0 0 0 0 9 25 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 13 21 2 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 2 0 0 0 0 21 25 1 0 0 0 0 21 28 1 0 0 0 0 22 24 2 0 0 0 0 23 24 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.2
Volume:	426.719
LogP:	6.43
LogD:	4.028
LogS:	-4.72
# Rotatable Bonds:	4
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	3.413
Fsp3:	0.36
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:	-4.78
MDCK Permeability:	1.4836237824056298e-05
Pgp-inhibitor:	0.203
Pgp-substrate:	0.677
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.126

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	92.72628021240234%
Volume Distribution (VD):	1.007
Pgp-substrate:	4.252298355102539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.856
CYP1A2-substrate:	0.464
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.784
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.338
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	14.776
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.813
Drug-inuced Liver Injury (DILI):	0.593
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.456
Skin Sensitization:	0.334
Carcinogencity:	0.513
Eye Corrosion:	0.006
Eye Irritation:	0.923
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC12070

Natural Product ID:	NPC12070
*Common Name:**	Vismin
IUPAC Name:	n.a.
Synonyms:	Vismin
Standard InCHIKey:	YMNIXNKCFMKXSJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H28O4/c1-14(2)6-8-25(9-7-15(3)4)18-12-17-10-16(5)11-19(26)22(17)24(29)23(18)20(27)13-21(25)28/h6-7,10-13,26,28-29H,8-9H2,1-5H3
SMILES:	CC(=CCC1(CC=C(C)C)C(=CC(=O)c2c1cc1cc(C)cc(c1c2O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467416
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828475]
NPO3648	Pittocaulon velatum	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[21661732]
NPO3648	Pittocaulon velatum	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[21661732]
NPO22183	Dryobalanops oblongifolia	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3648	Pittocaulon velatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13132	Genista corsica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17693	Forcipomyia marksae	Species	Ceratopogonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16833	Nauclea pilosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16068	Berberis stolonifera	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13828	Achillea santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17772	Piper nepalense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22183	Dryobalanops oblongifolia	Species	Dipterocarpaceae	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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5.2	ug.mL-1	PMID[536294]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	7.3	ug.mL-1	PMID[536294]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	5.7	ug.mL-1	PMID[536294]

☑ 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 NPC12070 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	367
0.1-0.2	1573
0.2-0.3	3398
0.3-0.4	9140
0.4-0.5	10397
0.5-0.6	5347
0.6-0.7	7050
0.7-0.8	4718
0.8-0.85	502
0.85-0.9	178
0.9-0.95	21
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC249272
0.9921	High Similarity	NPC114183
0.9844	High Similarity	NPC270899
0.9769	High Similarity	NPC53001
0.9695	High Similarity	NPC87723
0.9248	High Similarity	NPC191976
0.9219	High Similarity	NPC160499
0.9167	High Similarity	NPC267205
0.9065	High Similarity	NPC12402
0.9044	High Similarity	NPC138099
0.9044	High Similarity	NPC242994
0.9037	High Similarity	NPC471905
0.8978	High Similarity	NPC181560
0.8978	High Similarity	NPC169452
0.8963	High Similarity	NPC118919
0.8963	High Similarity	NPC254847
0.8955	High Similarity	NPC282780
0.8955	High Similarity	NPC166480
0.8947	High Similarity	NPC175738
0.8931	High Similarity	NPC48248
0.8923	High Similarity	NPC254492
0.8921	High Similarity	NPC296752
0.8915	High Similarity	NPC173978
0.8913	High Similarity	NPC246638
0.8913	High Similarity	NPC110810
0.8897	High Similarity	NPC53206
0.8897	High Similarity	NPC53414
0.8889	High Similarity	NPC290803
0.8889	High Similarity	NPC283088
0.8872	High Similarity	NPC17083
0.8864	High Similarity	NPC276238
0.8864	High Similarity	NPC92624
0.8864	High Similarity	NPC109123
0.8857	High Similarity	NPC227841
0.8855	High Similarity	NPC72667
0.8849	High Similarity	NPC193555
0.8849	High Similarity	NPC474961
0.8849	High Similarity	NPC135524
0.8815	High Similarity	NPC50924
0.8815	High Similarity	NPC475088
0.8806	High Similarity	NPC58685
0.8797	High Similarity	NPC259942
0.8788	High Similarity	NPC96024
0.8788	High Similarity	NPC282923
0.8786	High Similarity	NPC174905
0.8786	High Similarity	NPC163948
0.8786	High Similarity	NPC474203
0.8786	High Similarity	NPC295712
0.8786	High Similarity	NPC451542
0.8786	High Similarity	NPC293545
0.8786	High Similarity	NPC313047
0.8777	High Similarity	NPC204045
0.8777	High Similarity	NPC305845
0.8769	High Similarity	NPC199273
0.8768	High Similarity	NPC143438
0.8741	High Similarity	NPC225051
0.8741	High Similarity	NPC37299
0.8741	High Similarity	NPC115458
0.8741	High Similarity	NPC180261
0.8732	High Similarity	NPC143685
0.8731	High Similarity	NPC474517
0.8731	High Similarity	NPC72669
0.8731	High Similarity	NPC41847
0.8722	High Similarity	NPC303910
0.8722	High Similarity	NPC171460
0.8722	High Similarity	NPC146647
0.8722	High Similarity	NPC34414
0.8712	High Similarity	NPC84672
0.8712	High Similarity	NPC176130
0.8712	High Similarity	NPC78364
0.8712	High Similarity	NPC471530
0.8712	High Similarity	NPC69424
0.8705	High Similarity	NPC168471
0.8702	High Similarity	NPC477454
0.8676	High Similarity	NPC44437
0.8676	High Similarity	NPC287604
0.8676	High Similarity	NPC472262
0.8676	High Similarity	NPC161964
0.8671	High Similarity	NPC37709
0.8671	High Similarity	NPC290194
0.8671	High Similarity	NPC34802
0.8662	High Similarity	NPC34482
0.8657	High Similarity	NPC55949
0.8652	High Similarity	NPC84266
0.8652	High Similarity	NPC471682
0.8636	High Similarity	NPC473691
0.8636	High Similarity	NPC267846
0.8636	High Similarity	NPC3224
0.8633	High Similarity	NPC190457
0.8623	High Similarity	NPC245923
0.8613	High Similarity	NPC161632
0.8603	High Similarity	NPC314048
0.8603	High Similarity	NPC48036
0.8601	High Similarity	NPC470570
0.8593	High Similarity	NPC244699
0.8593	High Similarity	NPC205992
0.8592	High Similarity	NPC21599
0.8592	High Similarity	NPC244691
0.8592	High Similarity	NPC193703
0.8592	High Similarity	NPC471906
0.8592	High Similarity	NPC48762
0.8592	High Similarity	NPC10764
0.8582	High Similarity	NPC182255
0.8582	High Similarity	NPC278928
0.8582	High Similarity	NPC239136
0.8582	High Similarity	NPC99731
0.8582	High Similarity	NPC19631
0.8582	High Similarity	NPC474998
0.8582	High Similarity	NPC94076
0.8582	High Similarity	NPC257644
0.8571	High Similarity	NPC162612
0.8571	High Similarity	NPC100067
0.8571	High Similarity	NPC23126
0.8571	High Similarity	NPC266689
0.8571	High Similarity	NPC169250
0.8571	High Similarity	NPC116513
0.8571	High Similarity	NPC103356
0.8571	High Similarity	NPC315578
0.8571	High Similarity	NPC98254
0.8571	High Similarity	NPC105157
0.8571	High Similarity	NPC190043
0.8571	High Similarity	NPC30501
0.8571	High Similarity	NPC72158
0.8561	High Similarity	NPC4214
0.8561	High Similarity	NPC103540
0.8561	High Similarity	NPC473622
0.8561	High Similarity	NPC13715
0.8552	High Similarity	NPC97028
0.8552	High Similarity	NPC329933
0.8552	High Similarity	NPC288036
0.8552	High Similarity	NPC158338
0.8552	High Similarity	NPC65589
0.8552	High Similarity	NPC97029
0.8552	High Similarity	NPC100985
0.8551	High Similarity	NPC474813
0.8551	High Similarity	NPC315275
0.8551	High Similarity	NPC272268
0.8551	High Similarity	NPC474311
0.8551	High Similarity	NPC472308
0.8551	High Similarity	NPC155211
0.854	High Similarity	NPC474519
0.8538	High Similarity	NPC154696
0.8531	High Similarity	NPC471683
0.8529	High Similarity	NPC70622
0.8519	High Similarity	NPC31799
0.8519	High Similarity	NPC108129
0.8519	High Similarity	NPC62219
0.8511	High Similarity	NPC290550
0.8511	High Similarity	NPC187843
0.8507	High Similarity	NPC21305
0.8507	High Similarity	NPC221777
0.8507	High Similarity	NPC473017
0.85	High Similarity	NPC162939
0.85	High Similarity	NPC26924
0.8496	Intermediate Similarity	NPC62952
0.8496	Intermediate Similarity	NPC231774
0.8493	Intermediate Similarity	NPC205766
0.8489	Intermediate Similarity	NPC471452
0.8489	Intermediate Similarity	NPC305060
0.8489	Intermediate Similarity	NPC36868
0.8489	Intermediate Similarity	NPC62272
0.8489	Intermediate Similarity	NPC290030
0.8485	Intermediate Similarity	NPC142956
0.8485	Intermediate Similarity	NPC236189
0.8483	Intermediate Similarity	NPC256672
0.8483	Intermediate Similarity	NPC27221
0.8483	Intermediate Similarity	NPC7025
0.8478	Intermediate Similarity	NPC80035
0.8473	Intermediate Similarity	NPC91105
0.8473	Intermediate Similarity	NPC176208
0.8473	Intermediate Similarity	NPC307174
0.8473	Intermediate Similarity	NPC282577
0.8472	Intermediate Similarity	NPC271944
0.8472	Intermediate Similarity	NPC110882
0.8472	Intermediate Similarity	NPC85393
0.8467	Intermediate Similarity	NPC53896
0.8456	Intermediate Similarity	NPC471851
0.8451	Intermediate Similarity	NPC73061
0.844	Intermediate Similarity	NPC96421
0.8435	Intermediate Similarity	NPC72958
0.8435	Intermediate Similarity	NPC149526
0.8435	Intermediate Similarity	NPC232645
0.8435	Intermediate Similarity	NPC474417
0.8435	Intermediate Similarity	NPC35
0.8429	Intermediate Similarity	NPC416
0.8429	Intermediate Similarity	NPC230811
0.8429	Intermediate Similarity	NPC61398
0.8425	Intermediate Similarity	NPC477221
0.8421	Intermediate Similarity	NPC475733
0.8421	Intermediate Similarity	NPC10926
0.8417	Intermediate Similarity	NPC65005
0.8417	Intermediate Similarity	NPC194764
0.8417	Intermediate Similarity	NPC264112
0.8414	Intermediate Similarity	NPC245584
0.8414	Intermediate Similarity	NPC7943
0.8414	Intermediate Similarity	NPC56433
0.8414	Intermediate Similarity	NPC118027
0.8414	Intermediate Similarity	NPC190648
0.8414	Intermediate Similarity	NPC289042
0.8414	Intermediate Similarity	NPC312929

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 NPC12070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	961
0.2-0.3	1406
0.3-0.4	2705
0.4-0.5	2193
0.5-0.6	1102
0.6-0.7	352
0.7-0.8	97
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD1509	Clinical (unspecified phase)
0.8857	High Similarity	NPD7390	Discontinued
0.8682	High Similarity	NPD1201	Approved
0.8561	High Similarity	NPD1470	Approved
0.8489	Intermediate Similarity	NPD5405	Approved
0.8489	Intermediate Similarity	NPD5406	Approved
0.8489	Intermediate Similarity	NPD5404	Approved
0.8489	Intermediate Similarity	NPD5408	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.7939	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6959	Discontinued
0.7836	Intermediate Similarity	NPD2932	Approved
0.7834	Intermediate Similarity	NPD6232	Discontinued
0.7799	Intermediate Similarity	NPD7473	Discontinued
0.7785	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3300	Phase 2
0.7762	Intermediate Similarity	NPD1607	Approved
0.7761	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1164	Approved
0.7727	Intermediate Similarity	NPD7819	Suspended
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD6099	Approved
0.7704	Intermediate Similarity	NPD3019	Approved
0.7697	Intermediate Similarity	NPD3226	Approved
0.7671	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD2533	Approved
0.7667	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD2532	Approved
0.7655	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1510	Phase 2
0.7622	Intermediate Similarity	NPD1240	Approved
0.7619	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD2800	Approved
0.755	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4750	Phase 3
0.7519	Intermediate Similarity	NPD5951	Approved
0.7517	Intermediate Similarity	NPD6651	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4380	Phase 2
0.7415	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3750	Approved
0.74	Intermediate Similarity	NPD7003	Approved
0.7385	Intermediate Similarity	NPD2342	Discontinued
0.7383	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD7635	Approved
0.7368	Intermediate Similarity	NPD1511	Approved
0.7325	Intermediate Similarity	NPD1934	Approved
0.7324	Intermediate Similarity	NPD2798	Approved
0.7319	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6599	Discontinued
0.7292	Intermediate Similarity	NPD4625	Phase 3
0.7278	Intermediate Similarity	NPD2801	Approved
0.7273	Intermediate Similarity	NPD1512	Approved
0.7266	Intermediate Similarity	NPD3023	Approved
0.7266	Intermediate Similarity	NPD3026	Approved
0.7261	Intermediate Similarity	NPD7411	Suspended
0.725	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD7075	Discontinued
0.7248	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD3024	Approved
0.7246	Intermediate Similarity	NPD3025	Approved
0.7244	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8150	Discontinued
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2344	Approved
0.7197	Intermediate Similarity	NPD74	Approved
0.7197	Intermediate Similarity	NPD9266	Approved
0.7195	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7768	Phase 2
0.7181	Intermediate Similarity	NPD2799	Discontinued
0.717	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5844	Phase 1
0.7169	Intermediate Similarity	NPD6020	Phase 2
0.7163	Intermediate Similarity	NPD3972	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7123	Intermediate Similarity	NPD3764	Approved
0.7123	Intermediate Similarity	NPD2313	Discontinued
0.7122	Intermediate Similarity	NPD1651	Approved
0.7121	Intermediate Similarity	NPD9263	Approved
0.7121	Intermediate Similarity	NPD9264	Approved
0.7121	Intermediate Similarity	NPD9267	Approved
0.7105	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3882	Suspended
0.7073	Intermediate Similarity	NPD5711	Approved
0.7073	Intermediate Similarity	NPD5710	Approved
0.7071	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3748	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7019	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1203	Approved
0.7013	Intermediate Similarity	NPD2309	Approved
0.7007	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD6801	Discontinued
0.6993	Remote Similarity	NPD1243	Approved
0.6993	Remote Similarity	NPD1755	Approved
0.6988	Remote Similarity	NPD6166	Phase 2
0.6988	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6663	Approved
0.6954	Remote Similarity	NPD4308	Phase 3
0.6954	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5494	Approved
0.6948	Remote Similarity	NPD8166	Discontinued
0.6948	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7008	Discontinued
0.6933	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9269	Phase 2
0.6923	Remote Similarity	NPD6799	Approved
0.6918	Remote Similarity	NPD5736	Approved
0.6914	Remote Similarity	NPD3817	Phase 2
0.6905	Remote Similarity	NPD7177	Discontinued
0.6897	Remote Similarity	NPD2797	Approved
0.6892	Remote Similarity	NPD411	Approved
0.6892	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9281	Approved
0.6879	Remote Similarity	NPD9268	Approved
0.6875	Remote Similarity	NPD4749	Approved
0.6875	Remote Similarity	NPD844	Approved
0.6866	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1471	Phase 3
0.686	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD8313	Approved
0.6853	Remote Similarity	NPD1281	Approved
0.6852	Remote Similarity	NPD1465	Phase 2
0.6842	Remote Similarity	NPD5029	Approved
0.6842	Remote Similarity	NPD5027	Approved
0.6842	Remote Similarity	NPD5031	Approved
0.6831	Remote Similarity	NPD4626	Approved
0.6824	Remote Similarity	NPD7074	Phase 3
0.6822	Remote Similarity	NPD288	Approved
0.6818	Remote Similarity	NPD9261	Approved
0.6809	Remote Similarity	NPD3091	Approved
0.6806	Remote Similarity	NPD9717	Approved
0.6806	Remote Similarity	NPD4878	Approved
0.6806	Remote Similarity	NPD1608	Approved
0.6805	Remote Similarity	NPD3818	Discontinued
0.6802	Remote Similarity	NPD5028	Approved
0.6802	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4955	Approved
0.6802	Remote Similarity	NPD5026	Approved
0.6802	Remote Similarity	NPD36	Approved
0.6802	Remote Similarity	NPD4954	Approved
0.6802	Remote Similarity	NPD5034	Approved
0.6798	Remote Similarity	NPD6534	Approved
0.6798	Remote Similarity	NPD6535	Approved
0.6794	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3094	Phase 2
0.6768	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7054	Approved
0.6763	Remote Similarity	NPD497	Approved
0.6757	Remote Similarity	NPD6832	Phase 2
0.6755	Remote Similarity	NPD230	Phase 1
0.6744	Remote Similarity	NPD5030	Phase 2
0.6744	Remote Similarity	NPD1809	Phase 2
0.6743	Remote Similarity	NPD5037	Approved
0.6743	Remote Similarity	NPD5038	Approved
0.6742	Remote Similarity	NPD6213	Phase 3
0.6742	Remote Similarity	NPD6212	Phase 3
0.6742	Remote Similarity	NPD846	Approved
0.6742	Remote Similarity	NPD940	Approved
0.6742	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3092	Approved
0.6736	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3400	Discontinued
0.673	Remote Similarity	NPD6273	Approved
0.6725	Remote Similarity	NPD7472	Approved
0.6718	Remote Similarity	NPD3020	Approved
0.6715	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4059	Approved
0.6713	Remote Similarity	NPD2286	Discontinued
0.6712	Remote Similarity	NPD6696	Suspended
0.6707	Remote Similarity	NPD5402	Approved
0.6703	Remote Similarity	NPD6777	Approved
0.6703	Remote Similarity	NPD6781	Approved
0.6703	Remote Similarity	NPD6779	Approved
0.6703	Remote Similarity	NPD6780	Approved
0.6703	Remote Similarity	NPD6778	Approved
0.6703	Remote Similarity	NPD6782	Approved
0.6703	Remote Similarity	NPD6776	Approved
0.6692	Remote Similarity	NPD1930	Approved
0.6692	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1929	Approved
0.6692	Remote Similarity	NPD3495	Discontinued
0.6691	Remote Similarity	NPD498	Approved
0.6691	Remote Similarity	NPD496	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