NPASS Compound

Structure

CID195167 OpenBabel06191715582D 28 33 0 0 1 0 0 0 0 0999 V2000 -2.3515 1.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3582 0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5601 1.8272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5734 0.0071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3298 -1.3629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5543 -0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1188 -0.0198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0186 2.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1411 2.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1120 -0.9191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7753 1.3664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5611 -0.0081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3433 0.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0113 1.8127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8008 3.1544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1462 1.7850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 3.1515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7819 0.4564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3596 1.3388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7912 1.3489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5844 2.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5734 1.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7865 0.4463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8911 -1.3768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8028 4.0584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9286 1.3323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3796 4.0554 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 18 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 13 19 1 0 0 0 0 14 8 1 1 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 25 2 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 22 2 0 0 0 0 20 22 1 1 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 23 12 1 6 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.1
Volume:	372.612
LogP:	4.77
LogD:	3.249
LogS:	-5.503
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	3.885
Fsp3:	0.174
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.302
MDCK Permeability:	7.513537639169954e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.204
20% Bioavailability (F20%):	0.736
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	98.5229263305664%
Volume Distribution (VD):	0.481
Pgp-substrate:	1.6975128650665283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.643
CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.893
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.799
CYP2D6-substrate:	0.504
CYP3A4-inhibitor:	0.42
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	5.443
Half-life (T1/2):	0.168

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.875
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.801
Carcinogencity:	0.513
Eye Corrosion:	0.003
Eye Irritation:	0.488
Respiratory Toxicity:	0.312

Download Data

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

Natural Product: NPC195167

Natural Product ID:	NPC195167
*Common Name:**	Ohioensin H
IUPAC Name:	n.a.
Synonyms:	Ohioensin H
Standard InCHIKey:	QPKCEEFQPFTYIX-IJIZOXLDSA-N
Standard InCHI:	InChI=1S/C23H16O5/c24-10-5-6-12-13(7-10)19-16(26)9-17(27)21-15(25)8-14-11-3-1-2-4-18(11)28-23(12)20(14)22(19)21/h1-7,9,14,20,23-24,26-27H,8H2/t14-,20+,23+/m1/s1
SMILES:	Oc1ccc2c(c1)c1c(O)cc(c3c1[C@H]1[C@H]2Oc2ccccc2[C@H]1CC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562512
PubChem CID:	44233687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans

*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
NPO23276	Flavoparmelia euplecta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650094]
NPO23405	Sidnyum turbinatum	n.a.	n.a.	n.a.	n.a.	Mediterranean	n.a.	PMID[11430005]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572610]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23451	Polytrichum commune	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20283	Croton ruizianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23276	Flavoparmelia euplecta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23951	Oxytropis muricata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23405	Sidnyum turbinatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4019	Anabaena laxa	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23997	Adesmia boronioides	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[495024]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[495024]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.13	ug.mL-1	PMID[495024]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	0.11	ug.mL-1	PMID[495024]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.0022	ug.mL-1	PMID[495024]

☑ 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 NPC195167 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	429
0.1-0.2	1751
0.2-0.3	3724
0.3-0.4	9492
0.4-0.5	8915
0.5-0.6	3519
0.6-0.7	5420
0.7-0.8	5641
0.8-0.85	2340
0.85-0.9	1236
0.9-0.95	220
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC292863
0.9934	High Similarity	NPC184326
0.9868	High Similarity	NPC18380
0.9868	High Similarity	NPC137232
0.974	High Similarity	NPC290160
0.9494	High Similarity	NPC300307
0.9423	High Similarity	NPC15374
0.9408	High Similarity	NPC87708
0.94	High Similarity	NPC35150
0.94	High Similarity	NPC106328
0.9375	High Similarity	NPC4200
0.9346	High Similarity	NPC121568
0.9342	High Similarity	NPC72958
0.9342	High Similarity	NPC232645
0.9286	High Similarity	NPC66441
0.9286	High Similarity	NPC300668
0.9286	High Similarity	NPC254351
0.9286	High Similarity	NPC182555
0.9286	High Similarity	NPC134171
0.9272	High Similarity	NPC122894
0.9236	High Similarity	NPC301256
0.9236	High Similarity	NPC312273
0.9231	High Similarity	NPC51760
0.9231	High Similarity	NPC105584
0.9231	High Similarity	NPC18699
0.9231	High Similarity	NPC55443
0.9231	High Similarity	NPC472617
0.9226	High Similarity	NPC69531
0.9226	High Similarity	NPC32867
0.9221	High Similarity	NPC329844
0.9216	High Similarity	NPC178484
0.9216	High Similarity	NPC316960
0.9216	High Similarity	NPC149526
0.9216	High Similarity	NPC148945
0.9216	High Similarity	NPC204561
0.9216	High Similarity	NPC474417
0.9216	High Similarity	NPC317715
0.9216	High Similarity	NPC78835
0.9216	High Similarity	NPC309512
0.9211	High Similarity	NPC3642
0.92	High Similarity	NPC39045
0.92	High Similarity	NPC470135
0.92	High Similarity	NPC470136
0.9182	High Similarity	NPC469664
0.9177	High Similarity	NPC473011
0.9177	High Similarity	NPC473012
0.9172	High Similarity	NPC472618
0.9172	High Similarity	NPC186325
0.9172	High Similarity	NPC226462
0.9172	High Similarity	NPC42965
0.9172	High Similarity	NPC195136
0.9172	High Similarity	NPC98023
0.9167	High Similarity	NPC257166
0.9167	High Similarity	NPC1796
0.9167	High Similarity	NPC475184
0.9156	High Similarity	NPC39154
0.9156	High Similarity	NPC174086
0.9156	High Similarity	NPC78324
0.9156	High Similarity	NPC115601
0.9156	High Similarity	NPC208011
0.9139	High Similarity	NPC470132
0.9139	High Similarity	NPC470133
0.9139	High Similarity	NPC470131
0.9139	High Similarity	NPC109183
0.9139	High Similarity	NPC470134
0.9139	High Similarity	NPC473078
0.9125	High Similarity	NPC251336
0.9125	High Similarity	NPC477835
0.9119	High Similarity	NPC473009
0.9114	High Similarity	NPC273467
0.9114	High Similarity	NPC189552
0.9108	High Similarity	NPC15815
0.9108	High Similarity	NPC177650
0.9108	High Similarity	NPC51247
0.9108	High Similarity	NPC295090
0.9097	High Similarity	NPC169990
0.9097	High Similarity	NPC210942
0.9091	High Similarity	NPC478148
0.9085	High Similarity	NPC158338
0.9085	High Similarity	NPC65589
0.9085	High Similarity	NPC473016
0.9085	High Similarity	NPC132345
0.9085	High Similarity	NPC97028
0.9085	High Similarity	NPC100985
0.9085	High Similarity	NPC97029
0.9085	High Similarity	NPC329933
0.9085	High Similarity	NPC288036
0.9073	High Similarity	NPC271288
0.9062	High Similarity	NPC473010
0.9051	High Similarity	NPC312993
0.9045	High Similarity	NPC322459
0.9045	High Similarity	NPC318527
0.9045	High Similarity	NPC323627
0.9045	High Similarity	NPC208258
0.9045	High Similarity	NPC324358
0.9045	High Similarity	NPC272196
0.9038	High Similarity	NPC66508
0.9038	High Similarity	NPC37253
0.9038	High Similarity	NPC226656
0.9038	High Similarity	NPC201227
0.9038	High Similarity	NPC79375
0.9038	High Similarity	NPC258474
0.9032	High Similarity	NPC154683
0.9032	High Similarity	NPC40356
0.9026	High Similarity	NPC472633
0.902	High Similarity	NPC7025
0.902	High Similarity	NPC256672
0.902	High Similarity	NPC27221
0.9013	High Similarity	NPC290133
0.9013	High Similarity	NPC24136
0.9013	High Similarity	NPC187282
0.9013	High Similarity	NPC228779
0.9007	High Similarity	NPC278249
0.9007	High Similarity	NPC77794
0.9007	High Similarity	NPC107177
0.9007	High Similarity	NPC125894
0.9007	High Similarity	NPC223812
0.9007	High Similarity	NPC85162
0.9007	High Similarity	NPC81697
0.9006	High Similarity	NPC320741
0.9006	High Similarity	NPC171985
0.9006	High Similarity	NPC224851
0.8987	High Similarity	NPC324736
0.8987	High Similarity	NPC186113
0.8981	High Similarity	NPC208152
0.8981	High Similarity	NPC78492
0.8981	High Similarity	NPC198489
0.8981	High Similarity	NPC309648
0.8981	High Similarity	NPC61112
0.8974	High Similarity	NPC71061
0.8974	High Similarity	NPC303485
0.8974	High Similarity	NPC290830
0.8974	High Similarity	NPC72425
0.8974	High Similarity	NPC194593
0.8968	High Similarity	NPC138299
0.8968	High Similarity	NPC305965
0.8968	High Similarity	NPC222713
0.8968	High Similarity	NPC67322
0.8968	High Similarity	NPC111112
0.8954	High Similarity	NPC473077
0.8954	High Similarity	NPC300988
0.8954	High Similarity	NPC22005
0.8954	High Similarity	NPC296998
0.8954	High Similarity	NPC34802
0.8954	High Similarity	NPC308200
0.8954	High Similarity	NPC7943
0.8954	High Similarity	NPC123202
0.8954	High Similarity	NPC10990
0.8947	High Similarity	NPC473014
0.8947	High Similarity	NPC473013
0.8947	High Similarity	NPC235217
0.8947	High Similarity	NPC131579
0.8947	High Similarity	NPC473015
0.8947	High Similarity	NPC131568
0.8944	High Similarity	NPC474591
0.894	High Similarity	NPC64915
0.894	High Similarity	NPC182852
0.894	High Similarity	NPC223500
0.894	High Similarity	NPC10937
0.894	High Similarity	NPC161506
0.894	High Similarity	NPC306829
0.894	High Similarity	NPC1089
0.894	High Similarity	NPC107572
0.894	High Similarity	NPC228504
0.894	High Similarity	NPC37496
0.894	High Similarity	NPC166482
0.894	High Similarity	NPC66515
0.894	High Similarity	NPC148757
0.894	High Similarity	NPC324134
0.894	High Similarity	NPC78
0.894	High Similarity	NPC166934
0.894	High Similarity	NPC310340
0.894	High Similarity	NPC265040
0.894	High Similarity	NPC167624
0.894	High Similarity	NPC328164
0.894	High Similarity	NPC32739
0.894	High Similarity	NPC296917
0.894	High Similarity	NPC324436
0.894	High Similarity	NPC125855
0.894	High Similarity	NPC40833
0.894	High Similarity	NPC76338
0.894	High Similarity	NPC227579
0.894	High Similarity	NPC177354
0.894	High Similarity	NPC194432
0.894	High Similarity	NPC220998
0.894	High Similarity	NPC76372
0.8938	High Similarity	NPC261896
0.8938	High Similarity	NPC473022
0.8931	High Similarity	NPC470342
0.8931	High Similarity	NPC121647
0.8931	High Similarity	NPC472060
0.8931	High Similarity	NPC472052
0.8924	High Similarity	NPC271741
0.8924	High Similarity	NPC287789
0.8917	High Similarity	NPC100049
0.8917	High Similarity	NPC150908
0.8917	High Similarity	NPC14606
0.8917	High Similarity	NPC265624
0.8917	High Similarity	NPC158027
0.8917	High Similarity	NPC205026

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 NPC195167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1007
0.2-0.3	1509
0.3-0.4	2604
0.4-0.5	1864
0.5-0.6	1074
0.6-0.7	474
0.7-0.8	165
0.8-0.85	37
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9359	High Similarity	NPD6959	Discontinued
0.9038	High Similarity	NPD8443	Clinical (unspecified phase)
0.8734	High Similarity	NPD2393	Clinical (unspecified phase)
0.8734	High Similarity	NPD7819	Suspended
0.8733	High Similarity	NPD1550	Clinical (unspecified phase)
0.8733	High Similarity	NPD1552	Clinical (unspecified phase)
0.8712	High Similarity	NPD7852	Clinical (unspecified phase)
0.8675	High Similarity	NPD1549	Phase 2
0.8608	High Similarity	NPD7411	Suspended
0.8581	High Similarity	NPD7410	Clinical (unspecified phase)
0.8581	High Similarity	NPD4378	Clinical (unspecified phase)
0.8544	High Similarity	NPD4380	Phase 2
0.8516	High Similarity	NPD7390	Discontinued
0.8509	High Similarity	NPD7768	Phase 2
0.8485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD6166	Phase 2
0.8485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3749	Approved
0.8443	Intermediate Similarity	NPD5844	Phase 1
0.8438	Intermediate Similarity	NPD1934	Approved
0.8434	Intermediate Similarity	NPD7473	Discontinued
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8301	Intermediate Similarity	NPD2796	Approved
0.8272	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5494	Approved
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3750	Approved
0.8198	Intermediate Similarity	NPD8312	Approved
0.8198	Intermediate Similarity	NPD8313	Approved
0.8194	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1511	Approved
0.8118	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2532	Approved
0.8113	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2534	Approved
0.8113	Intermediate Similarity	NPD2533	Approved
0.8105	Intermediate Similarity	NPD1607	Approved
0.8092	Intermediate Similarity	NPD1240	Approved
0.8081	Intermediate Similarity	NPD6559	Discontinued
0.8079	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7074	Phase 3
0.8063	Intermediate Similarity	NPD1512	Approved
0.8049	Intermediate Similarity	NPD2801	Approved
0.8025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7975	Intermediate Similarity	NPD7003	Approved
0.7965	Intermediate Similarity	NPD7472	Approved
0.7952	Intermediate Similarity	NPD3882	Suspended
0.7949	Intermediate Similarity	NPD5405	Approved
0.7949	Intermediate Similarity	NPD6099	Approved
0.7949	Intermediate Similarity	NPD5404	Approved
0.7949	Intermediate Similarity	NPD6100	Approved
0.7949	Intermediate Similarity	NPD5406	Approved
0.7949	Intermediate Similarity	NPD5408	Approved
0.7947	Intermediate Similarity	NPD4908	Phase 1
0.7919	Intermediate Similarity	NPD6797	Phase 2
0.7919	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3226	Approved
0.7885	Intermediate Similarity	NPD3748	Approved
0.7877	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7251	Discontinued
0.7866	Intermediate Similarity	NPD6599	Discontinued
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3818	Discontinued
0.7834	Intermediate Similarity	NPD1551	Phase 2
0.7829	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD6799	Approved
0.7824	Intermediate Similarity	NPD3787	Discontinued
0.7799	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD4625	Phase 3
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7727	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1465	Phase 2
0.7725	Intermediate Similarity	NPD8151	Discontinued
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7719	Intermediate Similarity	NPD7229	Phase 3
0.7697	Intermediate Similarity	NPD7458	Discontinued
0.7683	Intermediate Similarity	NPD5403	Approved
0.7679	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD2344	Approved
0.7658	Intermediate Similarity	NPD2799	Discontinued
0.7654	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7177	Discontinued
0.7643	Intermediate Similarity	NPD6651	Approved
0.764	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6273	Approved
0.7616	Intermediate Similarity	NPD5710	Approved
0.7616	Intermediate Similarity	NPD5711	Approved
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7870	Phase 2
0.7606	Intermediate Similarity	NPD7871	Phase 2
0.76	Intermediate Similarity	NPD1201	Approved
0.76	Intermediate Similarity	NPD1610	Phase 2
0.7596	Intermediate Similarity	NPD4363	Phase 3
0.7596	Intermediate Similarity	NPD4360	Phase 2
0.7581	Intermediate Similarity	NPD6778	Approved
0.7581	Intermediate Similarity	NPD6782	Approved
0.7581	Intermediate Similarity	NPD6777	Approved
0.7581	Intermediate Similarity	NPD6779	Approved
0.7581	Intermediate Similarity	NPD6781	Approved
0.7581	Intermediate Similarity	NPD6776	Approved
0.7581	Intermediate Similarity	NPD6780	Approved
0.7578	Intermediate Similarity	NPD1243	Approved
0.7576	Intermediate Similarity	NPD920	Approved
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5401	Approved
0.7561	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD1470	Approved
0.7515	Intermediate Similarity	NPD8455	Phase 2
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.7485	Intermediate Similarity	NPD2309	Approved
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4287	Approved
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7461	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7783	Phase 2
0.746	Intermediate Similarity	NPD7698	Approved
0.746	Intermediate Similarity	NPD7696	Phase 3
0.746	Intermediate Similarity	NPD7697	Approved
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD7199	Phase 2
0.7442	Intermediate Similarity	NPD919	Approved
0.7405	Intermediate Similarity	NPD943	Approved
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7394	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2313	Discontinued
0.7371	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7356	Intermediate Similarity	NPD1247	Approved
0.7353	Intermediate Similarity	NPD37	Approved
0.7345	Intermediate Similarity	NPD7228	Approved
0.7341	Intermediate Similarity	NPD6234	Discontinued
0.7326	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD4965	Approved
0.7326	Intermediate Similarity	NPD4967	Phase 2
0.7317	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.7312	Intermediate Similarity	NPD6535	Approved
0.7312	Intermediate Similarity	NPD6534	Approved
0.7308	Intermediate Similarity	NPD2861	Phase 2
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.7296	Intermediate Similarity	NPD1613	Approved
0.7296	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1203	Approved
0.7282	Intermediate Similarity	NPD7801	Approved
0.7278	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.7273	Intermediate Similarity	NPD4361	Phase 2
0.7273	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4288	Approved
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2798	Approved
0.7231	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7213	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5760	Phase 2
0.7209	Intermediate Similarity	NPD5761	Phase 2
0.7208	Intermediate Similarity	NPD1608	Approved
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7179	Intermediate Similarity	NPD2797	Approved
0.7171	Intermediate Similarity	NPD1651	Approved
0.716	Intermediate Similarity	NPD7427	Discontinued
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8319	Approved
0.715	Intermediate Similarity	NPD8320	Phase 1
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7089	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7212	Phase 2
0.7083	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7213	Phase 3
0.7081	Intermediate Similarity	NPD2979	Phase 3
0.7081	Intermediate Similarity	NPD8434	Phase 2
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)

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