NPASS Compound

Structure

CID146288 OpenBabel06191715502D 26 30 0 0 1 0 0 0 0 0999 V2000 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -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 1.8171 -1.1910 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 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 -2.6910 0.0000 C 0 0 0 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 4.4152 -1.6910 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 0 0 0 0 0 0 0 0 0 0 6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -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 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 7.0132 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 22 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 11 26 1 0 0 0 0 12 1 1 6 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 21 2 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.16
Volume:	359.329
LogP:	3.798
LogD:	3.366
LogS:	-3.266
# Rotatable Bonds:	2
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	3.408
Fsp3:	0.429
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:	-5.225
MDCK Permeability:	3.007820669154171e-05
Pgp-inhibitor:	0.698
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.486

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	94.1547622680664%
Volume Distribution (VD):	2.04
Pgp-substrate:	2.6867270469665527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.79
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.898
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	14.636
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.449
Rat Oral Acute Toxicity:	0.428
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.131
Carcinogencity:	0.882
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC146288

Natural Product ID:	NPC146288
*Common Name:**	Cavidine
IUPAC Name:	n.a.
Synonyms:	(+)-Cavidine; Cavidine
Standard InCHIKey:	JTZZGWPIBBTYNE-FKIZINRSSA-N
Standard InCHI:	InChI=1S/C21H23NO4/c1-12-14-4-5-17-21(26-11-25-17)16(14)10-22-7-6-13-8-18(23-2)19(24-3)9-15(13)20(12)22/h4-5,8-9,12,20H,6-7,10-11H2,1-3H3/t12-,20+/m0/s1
SMILES:	COc1cc2c(cc1OC)CCN1[C@@H]2[C@@H](C)c2c(C1)c1OCOc1cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453544
PubChem CID:	193148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO40821	Corydalis meifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619883]
NPO40821	Corydalis meifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631434]

☑ 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	2
Others	4

Activity Type	# Activity
Tissue	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	84.0	%	PMID[546167]
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	100.0	%	PMID[546167]
NPT548	Tissue	Ileum	Cavia porcellus	IC50	=	0.5	ug.mL-1	PMID[546167]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	84.0	%	PMID[546168]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	100.0	%	PMID[546168]
NPT548	Tissue	Ileum	Cavia porcellus	IC50	=	0.5	ug.mL-1	PMID[546168]

☑ 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 NPC146288 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	311
0.1-0.2	1510
0.2-0.3	7570
0.3-0.4	10436
0.4-0.5	6522
0.5-0.6	11974
0.6-0.7	3336
0.7-0.8	632
0.8-0.85	243
0.85-0.9	115
0.9-0.95	41
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC216459
0.9932	High Similarity	NPC138487
0.9932	High Similarity	NPC41178
0.973	High Similarity	NPC234392
0.973	High Similarity	NPC31311
0.9527	High Similarity	NPC210148
0.9527	High Similarity	NPC233029
0.9521	High Similarity	NPC475959
0.9521	High Similarity	NPC7467
0.9477	High Similarity	NPC238530
0.9477	High Similarity	NPC276944
0.9477	High Similarity	NPC232514
0.9452	High Similarity	NPC476144
0.9452	High Similarity	NPC106295
0.9452	High Similarity	NPC16107
0.9452	High Similarity	NPC210437
0.9452	High Similarity	NPC51957
0.9272	High Similarity	NPC93593
0.9216	High Similarity	NPC111485
0.9178	High Similarity	NPC128019
0.9178	High Similarity	NPC476567
0.9178	High Similarity	NPC136860
0.9156	High Similarity	NPC477559
0.9156	High Similarity	NPC160298
0.9156	High Similarity	NPC266753
0.9156	High Similarity	NPC306902
0.9156	High Similarity	NPC232924
0.9119	High Similarity	NPC2314
0.9091	High Similarity	NPC477080
0.9045	High Similarity	NPC24264
0.9045	High Similarity	NPC476432
0.9041	High Similarity	NPC328750
0.9041	High Similarity	NPC188163
0.9041	High Similarity	NPC474915
0.9041	High Similarity	NPC213206
0.902	High Similarity	NPC278799
0.902	High Similarity	NPC207757
0.902	High Similarity	NPC54379
0.902	High Similarity	NPC193949
0.902	High Similarity	NPC5238
0.902	High Similarity	NPC295691
0.902	High Similarity	NPC204828
0.902	High Similarity	NPC127674
0.902	High Similarity	NPC184026
0.902	High Similarity	NPC110416
0.902	High Similarity	NPC39701
0.902	High Similarity	NPC2413
0.902	High Similarity	NPC172765
0.902	High Similarity	NPC276588
0.902	High Similarity	NPC469817
0.902	High Similarity	NPC249797
0.902	High Similarity	NPC189266
0.8987	High Similarity	NPC247389
0.8981	High Similarity	NPC167546
0.8981	High Similarity	NPC16805
0.8981	High Similarity	NPC225774
0.8981	High Similarity	NPC302527
0.8973	High Similarity	NPC314682
0.8924	High Similarity	NPC219341
0.8896	High Similarity	NPC78733
0.8889	High Similarity	NPC148898
0.8868	High Similarity	NPC210918
0.8868	High Similarity	NPC298979
0.8846	High Similarity	NPC106786
0.8834	High Similarity	NPC148693
0.8834	High Similarity	NPC118633
0.8834	High Similarity	NPC294790
0.8812	High Similarity	NPC241055
0.8808	High Similarity	NPC476151
0.8805	High Similarity	NPC304659
0.8805	High Similarity	NPC86144
0.8797	High Similarity	NPC59567
0.8788	High Similarity	NPC299990
0.8788	High Similarity	NPC73492
0.8767	High Similarity	NPC7018
0.8758	High Similarity	NPC151895
0.8758	High Similarity	NPC192768
0.8758	High Similarity	NPC88249
0.8758	High Similarity	NPC97221
0.8758	High Similarity	NPC220858
0.8742	High Similarity	NPC168409
0.8704	High Similarity	NPC19520
0.8704	High Similarity	NPC149090
0.8701	High Similarity	NPC81733
0.8701	High Similarity	NPC326316
0.8693	High Similarity	NPC477565
0.8693	High Similarity	NPC103379
0.8679	High Similarity	NPC189470
0.8675	High Similarity	NPC185838
0.8654	High Similarity	NPC187022
0.8654	High Similarity	NPC80129
0.8654	High Similarity	NPC76079
0.8642	High Similarity	NPC75958
0.8642	High Similarity	NPC6152
0.8631	High Similarity	NPC477259
0.8631	High Similarity	NPC169387
0.8627	High Similarity	NPC24233
0.8627	High Similarity	NPC147390
0.8627	High Similarity	NPC476571
0.8627	High Similarity	NPC428
0.8627	High Similarity	NPC135538
0.8627	High Similarity	NPC246587
0.8606	High Similarity	NPC114364
0.8606	High Similarity	NPC320223
0.8599	High Similarity	NPC247639
0.8599	High Similarity	NPC25084
0.8598	High Similarity	NPC199465
0.8598	High Similarity	NPC229166
0.8598	High Similarity	NPC128560
0.8571	High Similarity	NPC13916
0.8571	High Similarity	NPC264850
0.8571	High Similarity	NPC92541
0.8571	High Similarity	NPC219162
0.8562	High Similarity	NPC321505
0.8562	High Similarity	NPC179825
0.8562	High Similarity	NPC191376
0.8553	High Similarity	NPC215829
0.8553	High Similarity	NPC130926
0.8553	High Similarity	NPC97072
0.8544	High Similarity	NPC476572
0.8535	High Similarity	NPC99659
0.8535	High Similarity	NPC244112
0.8535	High Similarity	NPC325871
0.8529	High Similarity	NPC281581
0.8519	High Similarity	NPC100566
0.8519	High Similarity	NPC57812
0.8519	High Similarity	NPC474324
0.8516	High Similarity	NPC223125
0.8509	High Similarity	NPC24465
0.8509	High Similarity	NPC231198
0.8506	High Similarity	NPC130941
0.8506	High Similarity	NPC37144
0.8506	High Similarity	NPC59907
0.8503	High Similarity	NPC179704
0.8491	Intermediate Similarity	NPC216816
0.8485	Intermediate Similarity	NPC187678
0.848	Intermediate Similarity	NPC473716
0.848	Intermediate Similarity	NPC475597
0.8476	Intermediate Similarity	NPC65403
0.8466	Intermediate Similarity	NPC82533
0.8466	Intermediate Similarity	NPC290759
0.8466	Intermediate Similarity	NPC475845
0.8466	Intermediate Similarity	NPC266176
0.8466	Intermediate Similarity	NPC158148
0.8462	Intermediate Similarity	NPC476579
0.8462	Intermediate Similarity	NPC476568
0.8452	Intermediate Similarity	NPC248642
0.8452	Intermediate Similarity	NPC275132
0.8447	Intermediate Similarity	NPC320104
0.8443	Intermediate Similarity	NPC126284
0.8443	Intermediate Similarity	NPC27887
0.8442	Intermediate Similarity	NPC144863
0.8442	Intermediate Similarity	NPC253883
0.8442	Intermediate Similarity	NPC90844
0.8442	Intermediate Similarity	NPC95075
0.8431	Intermediate Similarity	NPC145304
0.843	Intermediate Similarity	NPC24260
0.8415	Intermediate Similarity	NPC311991
0.8415	Intermediate Similarity	NPC474708
0.8415	Intermediate Similarity	NPC152212
0.8408	Intermediate Similarity	NPC223124
0.8405	Intermediate Similarity	NPC190332
0.8405	Intermediate Similarity	NPC181653
0.8402	Intermediate Similarity	NPC156576
0.8395	Intermediate Similarity	NPC247972
0.8393	Intermediate Similarity	NPC32413
0.8393	Intermediate Similarity	NPC474506
0.8385	Intermediate Similarity	NPC24954
0.8383	Intermediate Similarity	NPC23219
0.8365	Intermediate Similarity	NPC126519
0.8365	Intermediate Similarity	NPC170503
0.8365	Intermediate Similarity	NPC203784
0.8364	Intermediate Similarity	NPC227060
0.8364	Intermediate Similarity	NPC317439
0.8364	Intermediate Similarity	NPC10908
0.8364	Intermediate Similarity	NPC76682
0.8364	Intermediate Similarity	NPC477640
0.8364	Intermediate Similarity	NPC198498
0.8364	Intermediate Similarity	NPC317145
0.8364	Intermediate Similarity	NPC225597
0.8364	Intermediate Similarity	NPC63646
0.8364	Intermediate Similarity	NPC115284
0.8364	Intermediate Similarity	NPC276890
0.8364	Intermediate Similarity	NPC470739
0.8356	Intermediate Similarity	NPC160193
0.8354	Intermediate Similarity	NPC58766
0.8354	Intermediate Similarity	NPC2295
0.8354	Intermediate Similarity	NPC477564
0.8354	Intermediate Similarity	NPC475686
0.8343	Intermediate Similarity	NPC116284
0.8333	Intermediate Similarity	NPC475393
0.8333	Intermediate Similarity	NPC470879
0.8333	Intermediate Similarity	NPC211296
0.8333	Intermediate Similarity	NPC244554
0.8333	Intermediate Similarity	NPC207824
0.8333	Intermediate Similarity	NPC267408
0.8333	Intermediate Similarity	NPC477258
0.8333	Intermediate Similarity	NPC60538
0.8333	Intermediate Similarity	NPC258695
0.8323	Intermediate Similarity	NPC112575

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 NPC146288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	740
0.2-0.3	982
0.3-0.4	1916
0.4-0.5	2668
0.5-0.6	1809
0.6-0.7	639
0.7-0.8	171
0.8-0.85	22
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9452	High Similarity	NPD4584	Approved
0.9041	High Similarity	NPD4664	Clinical (unspecified phase)
0.8654	High Similarity	NPD7298	Approved
0.8609	High Similarity	NPD5084	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD3641	Approved
0.8452	Intermediate Similarity	NPD3640	Phase 3
0.8452	Intermediate Similarity	NPD3639	Approved
0.8364	Intermediate Similarity	NPD8251	Approved
0.8364	Intermediate Similarity	NPD8252	Approved
0.8364	Intermediate Similarity	NPD8099	Discontinued
0.8354	Intermediate Similarity	NPD4773	Phase 2
0.8354	Intermediate Similarity	NPD4772	Phase 2
0.8344	Intermediate Similarity	NPD4017	Approved
0.8333	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD8156	Discontinued
0.8312	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6107	Approved
0.8101	Intermediate Similarity	NPD6031	Approved
0.8101	Intermediate Similarity	NPD6030	Approved
0.8037	Intermediate Similarity	NPD6788	Approved
0.8025	Intermediate Similarity	NPD3124	Discontinued
0.8024	Intermediate Similarity	NPD4481	Phase 3
0.8023	Intermediate Similarity	NPD8053	Approved
0.8023	Intermediate Similarity	NPD8054	Approved
0.8012	Intermediate Similarity	NPD4166	Phase 2
0.8	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD5718	Phase 2
0.7904	Intermediate Similarity	NPD3051	Approved
0.7882	Intermediate Similarity	NPD5312	Approved
0.7882	Intermediate Similarity	NPD5313	Approved
0.7881	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7280	Phase 3
0.7861	Intermediate Similarity	NPD7281	Phase 3
0.7857	Intermediate Similarity	NPD2969	Approved
0.7857	Intermediate Similarity	NPD2970	Approved
0.7833	Intermediate Similarity	NPD4420	Approved
0.7811	Intermediate Similarity	NPD2489	Approved
0.7811	Intermediate Similarity	NPD2898	Approved
0.7811	Intermediate Similarity	NPD27	Approved
0.7798	Intermediate Similarity	NPD4010	Discontinued
0.7792	Intermediate Similarity	NPD6895	Approved
0.7792	Intermediate Similarity	NPD6896	Approved
0.7785	Intermediate Similarity	NPD5241	Discontinued
0.7771	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7833	Phase 2
0.7771	Intermediate Similarity	NPD7831	Phase 2
0.776	Intermediate Similarity	NPD5005	Approved
0.776	Intermediate Similarity	NPD5006	Approved
0.775	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7802	Discontinued
0.7697	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6071	Discontinued
0.7688	Intermediate Similarity	NPD7598	Phase 2
0.7682	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2563	Approved
0.7651	Intermediate Similarity	NPD2560	Approved
0.7651	Intermediate Similarity	NPD5977	Approved
0.7651	Intermediate Similarity	NPD5978	Approved
0.7647	Intermediate Similarity	NPD4474	Approved
0.7647	Intermediate Similarity	NPD4475	Approved
0.7613	Intermediate Similarity	NPD2492	Phase 1
0.7597	Intermediate Similarity	NPD3109	Approved
0.7597	Intermediate Similarity	NPD3110	Approved
0.7595	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2977	Approved
0.759	Intermediate Similarity	NPD2978	Approved
0.7586	Intermediate Similarity	NPD6297	Approved
0.7579	Intermediate Similarity	NPD3815	Phase 1
0.7579	Intermediate Similarity	NPD3816	Phase 1
0.7578	Intermediate Similarity	NPD2420	Approved
0.7578	Intermediate Similarity	NPD2421	Approved
0.7561	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5604	Discontinued
0.7547	Intermediate Similarity	NPD5177	Phase 3
0.7546	Intermediate Similarity	NPD4727	Phase 1
0.7531	Intermediate Similarity	NPD1424	Approved
0.7527	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5754	Discontinued
0.75	Intermediate Similarity	NPD6748	Discontinued
0.75	Intermediate Similarity	NPD8095	Phase 1
0.747	Intermediate Similarity	NPD7110	Phase 1
0.747	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7310	Approved
0.7458	Intermediate Similarity	NPD2968	Approved
0.7458	Intermediate Similarity	NPD7312	Approved
0.7458	Intermediate Similarity	NPD2971	Approved
0.7458	Intermediate Similarity	NPD7311	Approved
0.7458	Intermediate Similarity	NPD7313	Approved
0.7453	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6851	Approved
0.7416	Intermediate Similarity	NPD7309	Approved
0.7416	Intermediate Similarity	NPD6618	Phase 2
0.7416	Intermediate Similarity	NPD6853	Approved
0.7407	Intermediate Similarity	NPD7124	Phase 2
0.7391	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7906	Approved
0.7374	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4578	Approved
0.736	Intermediate Similarity	NPD4577	Approved
0.7353	Intermediate Similarity	NPD4055	Discovery
0.7341	Intermediate Similarity	NPD6688	Approved
0.7341	Intermediate Similarity	NPD6687	Approved
0.7333	Intermediate Similarity	NPD4663	Approved
0.733	Intermediate Similarity	NPD3885	Approved
0.7329	Intermediate Similarity	NPD4237	Approved
0.7329	Intermediate Similarity	NPD4236	Phase 3
0.731	Intermediate Similarity	NPD7400	Phase 3
0.7303	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3845	Phase 1
0.7296	Intermediate Similarity	NPD4108	Discontinued
0.7293	Intermediate Similarity	NPD7291	Discontinued
0.7293	Intermediate Similarity	NPD3349	Phase 2
0.7289	Intermediate Similarity	NPD4210	Discontinued
0.7284	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5457	Discontinued
0.7263	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4098	Discontinued
0.7243	Intermediate Similarity	NPD5582	Discontinued
0.7229	Intermediate Similarity	NPD5976	Discontinued
0.7229	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4162	Approved
0.7219	Intermediate Similarity	NPD3383	Approved
0.7219	Intermediate Similarity	NPD3382	Approved
0.7219	Intermediate Similarity	NPD3384	Approved
0.7213	Intermediate Similarity	NPD2488	Approved
0.7213	Intermediate Similarity	NPD2490	Approved
0.7208	Intermediate Similarity	NPD7247	Discontinued
0.7207	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6875	Approved
0.7202	Intermediate Similarity	NPD6876	Approved
0.72	Intermediate Similarity	NPD2668	Approved
0.72	Intermediate Similarity	NPD2667	Approved
0.7193	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5283	Phase 1
0.7171	Intermediate Similarity	NPD2232	Approved
0.7171	Intermediate Similarity	NPD2233	Approved
0.7171	Intermediate Similarity	NPD2230	Approved
0.717	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6090	Discontinued
0.7168	Intermediate Similarity	NPD5677	Discontinued
0.7167	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7119	Phase 2
0.712	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3060	Approved
0.7111	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3705	Approved
0.7102	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4859	Phase 1
0.7097	Intermediate Similarity	NPD7905	Discontinued
0.7097	Intermediate Similarity	NPD6493	Phase 3
0.7089	Intermediate Similarity	NPD2674	Phase 3
0.7085	Intermediate Similarity	NPD3763	Approved
0.7083	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1753	Discontinued
0.7076	Intermediate Similarity	NPD5772	Approved
0.7076	Intermediate Similarity	NPD5773	Approved
0.7073	Intermediate Similarity	NPD6331	Phase 2
0.7069	Intermediate Similarity	NPD6037	Discontinued
0.7063	Intermediate Similarity	NPD2653	Approved
0.7055	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2238	Phase 2
0.7041	Intermediate Similarity	NPD4005	Discontinued
0.7039	Intermediate Similarity	NPD3920	Phase 2
0.7035	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5160	Discontinued
0.703	Intermediate Similarity	NPD3692	Discontinued
0.7025	Intermediate Similarity	NPD5111	Phase 2
0.7025	Intermediate Similarity	NPD3144	Approved
0.7025	Intermediate Similarity	NPD5110	Phase 2
0.7025	Intermediate Similarity	NPD3145	Approved
0.7025	Intermediate Similarity	NPD5109	Approved
0.7024	Intermediate Similarity	NPD2122	Discontinued
0.7024	Intermediate Similarity	NPD1914	Approved
0.7022	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2975	Approved
0.7021	Intermediate Similarity	NPD7034	Discontinued
0.7021	Intermediate Similarity	NPD2974	Approved
0.7021	Intermediate Similarity	NPD2973	Approved
0.7019	Intermediate Similarity	NPD2200	Suspended
0.7018	Intermediate Similarity	NPD5720	Discontinued
0.7013	Intermediate Similarity	NPD1421	Approved
0.7013	Intermediate Similarity	NPD1420	Approved
0.7	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4580	Approved
0.7	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3656	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