NPASS Compound

Structure

CID162193 OpenBabel06191715532D 23 27 0 0 1 0 0 0 0 0999 V2000 -5.1176 -0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5183 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 -0.9684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3569 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6784 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6785 1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0093 0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3571 -0.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6789 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 1.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5175 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 0.4846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8392 1.4540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8390 2.4540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2375 -1.4760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5176 1.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4396 1.7527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4393 0.1842 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 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 8 22 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 6 0 0 0 16 23 1 0 0 0 0 17 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	296.729
LogP:	2.67
LogD:	3.019
LogS:	-5.556
# Rotatable Bonds:	1
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.87
Synthetic Accessibility Score:	3.502
Fsp3:	0.294
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:	-4.996
MDCK Permeability:	3.508027657517232e-05
Pgp-inhibitor:	0.123
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	96.50982666015625%
Volume Distribution (VD):	0.809
Pgp-substrate:	2.8731689453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.688
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	6.525
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.637
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.965
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.127
Carcinogencity:	0.935
Eye Corrosion:	0.003
Eye Irritation:	0.506
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC162193

Natural Product ID:	NPC162193
*Common Name:**	LZMRDTLRSDRUSU-SJORKVTESA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Pisatin
Standard InCHIKey:	LZMRDTLRSDRUSU-SJORKVTESA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3/t16-,17+/m1/s1
SMILES:	COc1ccc2c(c1)OC[C@]1([C@@H]2Oc2c1cc1c(c2)OCO1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784262
PubChem CID:	101689
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
NPO21723	Jaborosa sativa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO21315	Adina polycephala	Species	Rubiaceae	Eukaryota	bark	n.a.	n.a.	PMID[18303851]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21510635]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	aerial parts	Limbe (South West) Province, Cameroon	2007-APR	PMID[21510635]
NPO21575	Lomatogonium rotatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2608753]
NPO8252	Filaginella uliginosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21181	Allia ramosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21047	Gardenia obtusifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20903	Sesbania drummondii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18728	Diplodia mutila	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21448	Argemone gracilenta	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21575	Lomatogonium rotatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21723	Jaborosa sativa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21315	Adina polycephala	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20098	Lasiocorys capensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27738	Diatraea grandiosella	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18182	Pisum fulvum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20509	Aconitum manshuricum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19834	Croton humilis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Inhibition	=	36.2	%	PMID[573728]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	>	5000000.0	nM	PMID[573728]

☑ 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 NPC162193 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	438
0.1-0.2	1660
0.2-0.3	4496
0.3-0.4	11231
0.4-0.5	7070
0.5-0.6	4389
0.6-0.7	6778
0.7-0.8	5079
0.8-0.85	1081
0.85-0.9	393
0.9-0.95	70
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC166584
0.9716	High Similarity	NPC301961
0.9643	High Similarity	NPC178014
0.9643	High Similarity	NPC42716
0.9643	High Similarity	NPC474749
0.9643	High Similarity	NPC11422
0.9574	High Similarity	NPC226540
0.9568	High Similarity	NPC174522
0.9496	High Similarity	NPC300798
0.9496	High Similarity	NPC58137
0.9452	High Similarity	NPC159922
0.9441	High Similarity	NPC71726
0.9429	High Similarity	NPC80326
0.9366	High Similarity	NPC307466
0.9362	High Similarity	NPC81638
0.9353	High Similarity	NPC292487
0.931	High Similarity	NPC238140
0.9241	High Similarity	NPC240521
0.9231	High Similarity	NPC180953
0.9225	High Similarity	NPC474808
0.9172	High Similarity	NPC175976
0.9155	High Similarity	NPC107161
0.9155	High Similarity	NPC472562
0.9149	High Similarity	NPC27495
0.911	High Similarity	NPC55158
0.911	High Similarity	NPC51328
0.911	High Similarity	NPC286235
0.9103	High Similarity	NPC227902
0.9097	High Similarity	NPC205316
0.9085	High Similarity	NPC247291
0.9078	High Similarity	NPC236306
0.9078	High Similarity	NPC9068
0.9078	High Similarity	NPC232164
0.9078	High Similarity	NPC473739
0.9071	High Similarity	NPC25695
0.9071	High Similarity	NPC172818
0.9041	High Similarity	NPC270751
0.9041	High Similarity	NPC248132
0.9041	High Similarity	NPC130449
0.9034	High Similarity	NPC190714
0.9034	High Similarity	NPC99515
0.9028	High Similarity	NPC280092
0.9028	High Similarity	NPC45257
0.9028	High Similarity	NPC93323
0.9028	High Similarity	NPC12641
0.9014	High Similarity	NPC184797
0.9014	High Similarity	NPC160283
0.9014	High Similarity	NPC254759
0.9014	High Similarity	NPC284464
0.9014	High Similarity	NPC177868
0.9014	High Similarity	NPC309124
0.9007	High Similarity	NPC474282
0.9007	High Similarity	NPC103976
0.9007	High Similarity	NPC102904
0.9007	High Similarity	NPC176051
0.9007	High Similarity	NPC107551
0.9007	High Similarity	NPC326797
0.8993	High Similarity	NPC58585
0.8973	High Similarity	NPC21776
0.8973	High Similarity	NPC39657
0.8973	High Similarity	NPC16269
0.8966	High Similarity	NPC18979
0.8966	High Similarity	NPC475096
0.8958	High Similarity	NPC102044
0.8958	High Similarity	NPC298317
0.8958	High Similarity	NPC47633
0.8958	High Similarity	NPC252169
0.8958	High Similarity	NPC255566
0.8958	High Similarity	NPC85264
0.8951	High Similarity	NPC471389
0.8944	High Similarity	NPC471388
0.8944	High Similarity	NPC127218
0.8944	High Similarity	NPC30951
0.8944	High Similarity	NPC319647
0.8944	High Similarity	NPC25966
0.8944	High Similarity	NPC292882
0.8944	High Similarity	NPC6369
0.8944	High Similarity	NPC245207
0.894	High Similarity	NPC189730
0.8936	High Similarity	NPC227503
0.8936	High Similarity	NPC173660
0.8936	High Similarity	NPC474639
0.8936	High Similarity	NPC197166
0.8936	High Similarity	NPC230734
0.8929	High Similarity	NPC474478
0.8919	High Similarity	NPC472709
0.8919	High Similarity	NPC98624
0.8919	High Similarity	NPC472710
0.8904	High Similarity	NPC112861
0.8904	High Similarity	NPC125755
0.8904	High Similarity	NPC33832
0.8897	High Similarity	NPC63879
0.8897	High Similarity	NPC25292
0.8897	High Similarity	NPC473045
0.8889	High Similarity	NPC246947
0.8889	High Similarity	NPC475084
0.8889	High Similarity	NPC41782
0.8889	High Similarity	NPC189115
0.8881	High Similarity	NPC226547
0.8874	High Similarity	NPC164152
0.8873	High Similarity	NPC185908
0.8873	High Similarity	NPC276490
0.8867	High Similarity	NPC78809
0.8865	High Similarity	NPC134968
0.8865	High Similarity	NPC112246
0.8865	High Similarity	NPC94750
0.8865	High Similarity	NPC474206
0.8865	High Similarity	NPC151224
0.8865	High Similarity	NPC112939
0.8865	High Similarity	NPC470356
0.8865	High Similarity	NPC195022
0.8865	High Similarity	NPC121812
0.8865	High Similarity	NPC61946
0.8857	High Similarity	NPC266848
0.8857	High Similarity	NPC215037
0.8857	High Similarity	NPC136750
0.8857	High Similarity	NPC263064
0.8851	High Similarity	NPC35877
0.8851	High Similarity	NPC95392
0.8851	High Similarity	NPC55715
0.8844	High Similarity	NPC116019
0.8844	High Similarity	NPC101376
0.8836	High Similarity	NPC22150
0.8836	High Similarity	NPC279298
0.8836	High Similarity	NPC43508
0.8836	High Similarity	NPC161700
0.8836	High Similarity	NPC38041
0.8836	High Similarity	NPC277867
0.8836	High Similarity	NPC476301
0.8836	High Similarity	NPC469586
0.8828	High Similarity	NPC12728
0.8828	High Similarity	NPC473044
0.8828	High Similarity	NPC477616
0.8828	High Similarity	NPC185071
0.8828	High Similarity	NPC46092
0.8819	High Similarity	NPC469661
0.8819	High Similarity	NPC311530
0.8811	High Similarity	NPC183781
0.8803	High Similarity	NPC248727
0.8803	High Similarity	NPC472334
0.8803	High Similarity	NPC16435
0.8803	High Similarity	NPC78047
0.8803	High Similarity	NPC306441
0.8803	High Similarity	NPC104167
0.8803	High Similarity	NPC472336
0.8803	High Similarity	NPC270456
0.8803	High Similarity	NPC269091
0.8803	High Similarity	NPC302701
0.8803	High Similarity	NPC162659
0.8803	High Similarity	NPC3049
0.8803	High Similarity	NPC265433
0.88	High Similarity	NPC302610
0.8794	High Similarity	NPC106215
0.8786	High Similarity	NPC65183
0.8786	High Similarity	NPC7744
0.8786	High Similarity	NPC72046
0.8786	High Similarity	NPC202762
0.8786	High Similarity	NPC261812
0.8786	High Similarity	NPC86655
0.8776	High Similarity	NPC324492
0.8776	High Similarity	NPC252286
0.8776	High Similarity	NPC317053
0.8776	High Similarity	NPC154971
0.8767	High Similarity	NPC469313
0.8767	High Similarity	NPC118385
0.8767	High Similarity	NPC84181
0.8767	High Similarity	NPC239254
0.8767	High Similarity	NPC283995
0.8767	High Similarity	NPC472713
0.8767	High Similarity	NPC187774
0.8767	High Similarity	NPC50250
0.8767	High Similarity	NPC472712
0.8767	High Similarity	NPC76176
0.8767	High Similarity	NPC217635
0.8767	High Similarity	NPC138227
0.8767	High Similarity	NPC473046
0.8767	High Similarity	NPC172171
0.8767	High Similarity	NPC79429
0.8767	High Similarity	NPC168579
0.8767	High Similarity	NPC471667
0.8767	High Similarity	NPC129417
0.8767	High Similarity	NPC470235
0.8759	High Similarity	NPC469559
0.8759	High Similarity	NPC302506
0.8759	High Similarity	NPC311057
0.8759	High Similarity	NPC472353
0.8758	High Similarity	NPC220462
0.875	High Similarity	NPC259519
0.875	High Similarity	NPC46591
0.8741	High Similarity	NPC474687
0.8741	High Similarity	NPC474039
0.8741	High Similarity	NPC211549
0.8741	High Similarity	NPC477938
0.8741	High Similarity	NPC283949
0.8732	High Similarity	NPC142547
0.8732	High Similarity	NPC150534
0.8732	High Similarity	NPC472337
0.8732	High Similarity	NPC126409
0.8732	High Similarity	NPC260898
0.8732	High Similarity	NPC99572

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 NPC162193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	925
0.2-0.3	1916
0.3-0.4	2768
0.4-0.5	1579
0.5-0.6	908
0.6-0.7	581
0.7-0.8	106
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD1612	Clinical (unspecified phase)
0.8652	High Similarity	NPD1613	Approved
0.85	High Similarity	NPD1529	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3027	Phase 3
0.8235	Intermediate Similarity	NPD1653	Approved
0.8228	Intermediate Similarity	NPD6234	Discontinued
0.8217	Intermediate Similarity	NPD4967	Phase 2
0.8217	Intermediate Similarity	NPD4966	Approved
0.8217	Intermediate Similarity	NPD4965	Approved
0.8125	Intermediate Similarity	NPD7199	Phase 2
0.8042	Intermediate Similarity	NPD2861	Phase 2
0.8025	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD1610	Phase 2
0.7988	Intermediate Similarity	NPD7228	Approved
0.7986	Intermediate Similarity	NPD4908	Phase 1
0.7947	Intermediate Similarity	NPD6674	Discontinued
0.7911	Intermediate Similarity	NPD1934	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3705	Approved
0.7872	Intermediate Similarity	NPD1091	Approved
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD7054	Approved
0.7714	Intermediate Similarity	NPD1548	Phase 1
0.7692	Intermediate Similarity	NPD7240	Approved
0.7687	Intermediate Similarity	NPD4625	Phase 3
0.7679	Intermediate Similarity	NPD7472	Approved
0.7677	Intermediate Similarity	NPD5058	Phase 3
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2801	Approved
0.764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4749	Approved
0.7628	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7551	Intermediate Similarity	NPD3018	Phase 2
0.7546	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7535	Intermediate Similarity	NPD1357	Approved
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7484	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7266	Discontinued
0.7442	Intermediate Similarity	NPD7549	Discontinued
0.744	Intermediate Similarity	NPD6166	Phase 2
0.744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3882	Suspended
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7421	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD2983	Phase 2
0.7394	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3817	Phase 2
0.7376	Intermediate Similarity	NPD6671	Approved
0.7375	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3384	Approved
0.7362	Intermediate Similarity	NPD3383	Approved
0.7362	Intermediate Similarity	NPD3382	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7355	Intermediate Similarity	NPD1375	Discontinued
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7329	Intermediate Similarity	NPD2981	Phase 2
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7296	Intermediate Similarity	NPD1511	Approved
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.7257	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5124	Phase 1
0.7255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5588	Approved
0.7214	Intermediate Similarity	NPD228	Approved
0.7212	Intermediate Similarity	NPD8455	Phase 2
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1512	Approved
0.7178	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4538	Approved
0.7161	Intermediate Similarity	NPD4536	Approved
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD4675	Approved
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4678	Approved
0.7124	Intermediate Similarity	NPD6233	Phase 2
0.7123	Intermediate Similarity	NPD5125	Phase 3
0.7123	Intermediate Similarity	NPD5126	Approved
0.7114	Intermediate Similarity	NPD8651	Approved
0.7114	Intermediate Similarity	NPD6696	Suspended
0.7108	Intermediate Similarity	NPD2977	Approved
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2978	Approved
0.7107	Intermediate Similarity	NPD7466	Approved
0.7105	Intermediate Similarity	NPD7095	Approved
0.7097	Intermediate Similarity	NPD7680	Approved
0.7089	Intermediate Similarity	NPD1549	Phase 2
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7081	Intermediate Similarity	NPD7212	Phase 2
0.7081	Intermediate Similarity	NPD7213	Phase 3
0.7078	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3620	Phase 2
0.7078	Intermediate Similarity	NPD1558	Phase 1
0.707	Intermediate Similarity	NPD3454	Phase 3
0.707	Intermediate Similarity	NPD6100	Approved
0.707	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD5402	Approved
0.7063	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7051	Intermediate Similarity	NPD7097	Phase 1
0.705	Intermediate Similarity	NPD290	Approved
0.7044	Intermediate Similarity	NPD5177	Phase 3
0.7039	Intermediate Similarity	NPD7906	Approved
0.7039	Intermediate Similarity	NPD6841	Approved
0.7039	Intermediate Similarity	NPD6842	Approved
0.7039	Intermediate Similarity	NPD6843	Phase 3
0.7037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7447	Phase 1
0.7032	Intermediate Similarity	NPD5735	Approved
0.703	Intermediate Similarity	NPD4380	Phase 2
0.7029	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD5762	Approved
0.7025	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3540	Phase 1
0.702	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6232	Discontinued
0.7014	Intermediate Similarity	NPD7157	Approved
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7006	Intermediate Similarity	NPD5960	Phase 3
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6331	Phase 2
0.7	Intermediate Similarity	NPD3892	Phase 2
0.7	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4110	Phase 3
0.7	Intermediate Similarity	NPD3750	Approved
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6988	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4663	Approved
0.6981	Remote Similarity	NPD2424	Discontinued
0.6978	Remote Similarity	NPD968	Approved
0.6977	Remote Similarity	NPD2969	Approved
0.6977	Remote Similarity	NPD2970	Approved
0.697	Remote Similarity	NPD4005	Discontinued
0.6964	Remote Similarity	NPD2563	Approved
0.6964	Remote Similarity	NPD2560	Approved
0.6962	Remote Similarity	NPD3539	Phase 1
0.6959	Remote Similarity	NPD1247	Approved
0.6959	Remote Similarity	NPD3496	Discontinued
0.6957	Remote Similarity	NPD2677	Approved
0.6944	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4237	Approved
0.6937	Remote Similarity	NPD4236	Phase 3
0.6933	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7028	Phase 2
0.6923	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD1933	Approved
0.6919	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD6071	Discontinued
0.6919	Remote Similarity	NPD3051	Approved
0.6914	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7313	Approved
0.691	Remote Similarity	NPD7311	Approved
0.691	Remote Similarity	NPD7312	Approved
0.691	Remote Similarity	NPD4577	Approved
0.691	Remote Similarity	NPD4578	Approved
0.691	Remote Similarity	NPD7310	Approved
0.6905	Remote Similarity	NPD5929	Approved
0.6899	Remote Similarity	NPD4108	Discontinued
0.6897	Remote Similarity	NPD7473	Discontinued
0.6894	Remote Similarity	NPD4628	Phase 3
0.689	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8054	Approved
0.6872	Remote Similarity	NPD7309	Approved
0.6872	Remote Similarity	NPD8053	Approved
0.6871	Remote Similarity	NPD6799	Approved
0.6871	Remote Similarity	NPD4357	Discontinued
0.6864	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2238	Phase 2
0.6855	Remote Similarity	NPD2796	Approved
0.6855	Remote Similarity	NPD2161	Phase 2
0.6852	Remote Similarity	NPD6190	Approved
0.6845	Remote Similarity	NPD6801	Discontinued
0.6842	Remote Similarity	NPD919	Approved
0.6839	Remote Similarity	NPD2489	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