NPASS Compound

Structure

NPC83198 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 2.3534 -2.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7618 -2.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1857 -1.9356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 1.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9031 -1.9356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2194 -0.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2194 -1.1413 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 2.3534 0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 -1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 -1.1413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6213 1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2618 -1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 -0.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9031 -0.6930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1857 -0.6930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 -1.6413 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2447 1.8587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4031 0.1730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 -1.3143 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 22 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 10 15 2 0 0 0 0 11 17 2 0 0 0 0 12 9 1 1 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.13
Volume:	315.997
LogP:	2.162
LogD:	2.068
LogS:	-2.645
# Rotatable Bonds:	1
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	3.208
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895
MDCK Permeability:	2.4064442186499946e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.59
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.216

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.879
Plasma Protein Binding (PPB):	69.1944808959961%
Volume Distribution (VD):	1.627
Pgp-substrate:	25.102436065673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.79
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.667
CYP2D6-inhibitor:	0.387
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.897

ADMET: Excretion

Clearance (CL):	14.261
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.15
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.933
Carcinogencity:	0.449
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC83198

Natural Product ID:	NPC83198
*Common Name:**	Claviculine
IUPAC Name:	n.a.
Synonyms:	Claviculine
Standard InCHIKey:	ZBTOEEFERPMYTH-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C18H19NO4/c1-19-8-7-10-3-5-13(20)18-15(10)12(19)9-11-4-6-14(22-2)16(21)17(11)23-18/h3-6,12,20-21H,7-9H2,1-2H3/t12-/m0/s1
SMILES:	COc1ccc2c(c1O)Oc1c(O)ccc3c1[C@H](C2)N(C)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452512
PubChem CID:	159034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002657] Cularin 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
NPO33048	sarcuapnos crassfolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8676127]

☑ 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	4
Others	2

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	IC50	=	1000.0	nM	PMID[574024]
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	1500.0	nM	PMID[574024]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	>	10000.0	nM	PMID[574024]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	>	100000.0	nM	PMID[574025]
NPT2	Others	Unspecified		Ratio IC50	<	0.01	n.a.	PMID[574025]
NPT2	Others	Unspecified		Ratio IC50	<	0.015	n.a.	PMID[574025]

☑ 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 NPC83198 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	351
0.1-0.2	1700
0.2-0.3	8688
0.3-0.4	9613
0.4-0.5	5139
0.5-0.6	8118
0.6-0.7	7138
0.7-0.8	1559
0.8-0.85	192
0.85-0.9	122
0.9-0.95	69
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC204908
0.981	High Similarity	NPC232386
0.981	High Similarity	NPC190783
0.981	High Similarity	NPC152680
0.9494	High Similarity	NPC13916
0.9494	High Similarity	NPC264850
0.943	High Similarity	NPC24465
0.9217	High Similarity	NPC258657
0.9217	High Similarity	NPC279228
0.9217	High Similarity	NPC15414
0.9217	High Similarity	NPC182052
0.9217	High Similarity	NPC104196
0.9217	High Similarity	NPC229373
0.9217	High Similarity	NPC285931
0.9217	High Similarity	NPC223690
0.9217	High Similarity	NPC42663
0.9217	High Similarity	NPC328155
0.9217	High Similarity	NPC8836
0.9217	High Similarity	NPC311973
0.9217	High Similarity	NPC222661
0.9217	High Similarity	NPC217748
0.9217	High Similarity	NPC7715
0.9217	High Similarity	NPC290005
0.9217	High Similarity	NPC54654
0.9217	High Similarity	NPC251735
0.9217	High Similarity	NPC271013
0.9217	High Similarity	NPC239824
0.9217	High Similarity	NPC290582
0.9217	High Similarity	NPC49075
0.9217	High Similarity	NPC185639
0.9217	High Similarity	NPC90998
0.9217	High Similarity	NPC181796
0.9172	High Similarity	NPC206900
0.9162	High Similarity	NPC274716
0.9162	High Similarity	NPC167116
0.9162	High Similarity	NPC254441
0.9157	High Similarity	NPC286119
0.9102	High Similarity	NPC30779
0.9053	High Similarity	NPC116465
0.9053	High Similarity	NPC212237
0.9032	High Similarity	NPC103379
0.9032	High Similarity	NPC477565
0.9024	High Similarity	NPC239775
0.9	High Similarity	NPC22115
0.9	High Similarity	NPC275680
0.8987	High Similarity	NPC2413
0.8987	High Similarity	NPC204828
0.8987	High Similarity	NPC207757
0.8987	High Similarity	NPC276588
0.8987	High Similarity	NPC110416
0.8987	High Similarity	NPC5238
0.8987	High Similarity	NPC184026
0.8987	High Similarity	NPC295691
0.8987	High Similarity	NPC469817
0.8987	High Similarity	NPC172765
0.8987	High Similarity	NPC127674
0.8987	High Similarity	NPC249797
0.8987	High Similarity	NPC54379
0.8987	High Similarity	NPC278799
0.8987	High Similarity	NPC39701
0.8987	High Similarity	NPC193949
0.8987	High Similarity	NPC189266
0.8968	High Similarity	NPC135538
0.8968	High Similarity	NPC476571
0.8968	High Similarity	NPC147390
0.8968	High Similarity	NPC24233
0.8968	High Similarity	NPC246587
0.8968	High Similarity	NPC428
0.8963	High Similarity	NPC118274
0.8963	High Similarity	NPC168753
0.8947	High Similarity	NPC48490
0.8947	High Similarity	NPC175890
0.8947	High Similarity	NPC11296
0.8947	High Similarity	NPC274661
0.8947	High Similarity	NPC82457
0.8903	High Similarity	NPC321505
0.8903	High Similarity	NPC476151
0.8903	High Similarity	NPC179825
0.8903	High Similarity	NPC191376
0.8895	High Similarity	NPC191132
0.8895	High Similarity	NPC60295
0.8882	High Similarity	NPC95426
0.8882	High Similarity	NPC16357
0.8882	High Similarity	NPC302245
0.8844	High Similarity	NPC24260
0.883	High Similarity	NPC139783
0.883	High Similarity	NPC65312
0.882	High Similarity	NPC329837
0.8805	High Similarity	NPC475557
0.8795	High Similarity	NPC76682
0.8795	High Similarity	NPC227060
0.8795	High Similarity	NPC198498
0.8795	High Similarity	NPC317439
0.8795	High Similarity	NPC317145
0.8795	High Similarity	NPC63646
0.8795	High Similarity	NPC10908
0.8795	High Similarity	NPC115284
0.8795	High Similarity	NPC276890
0.8793	High Similarity	NPC85381
0.8786	High Similarity	NPC41122
0.8786	High Similarity	NPC318805
0.8774	High Similarity	NPC185838
0.8757	High Similarity	NPC474507
0.8743	High Similarity	NPC41376
0.8743	High Similarity	NPC129518
0.8743	High Similarity	NPC251580
0.8743	High Similarity	NPC12424
0.8736	High Similarity	NPC478093
0.8734	High Similarity	NPC97221
0.8734	High Similarity	NPC151895
0.8734	High Similarity	NPC88249
0.8734	High Similarity	NPC192768
0.8734	High Similarity	NPC220858
0.8727	High Similarity	NPC117188
0.8727	High Similarity	NPC205421
0.8727	High Similarity	NPC145832
0.8727	High Similarity	NPC306555
0.8727	High Similarity	NPC474931
0.8727	High Similarity	NPC12053
0.8727	High Similarity	NPC158376
0.8727	High Similarity	NPC81218
0.872	High Similarity	NPC212794
0.872	High Similarity	NPC96603
0.872	High Similarity	NPC136508
0.872	High Similarity	NPC196447
0.872	High Similarity	NPC477563
0.872	High Similarity	NPC13504
0.872	High Similarity	NPC306843
0.872	High Similarity	NPC253043
0.872	High Similarity	NPC78222
0.8712	High Similarity	NPC60186
0.8693	High Similarity	NPC234318
0.8688	High Similarity	NPC2295
0.8688	High Similarity	NPC477564
0.8686	High Similarity	NPC478091
0.8686	High Similarity	NPC30182
0.8686	High Similarity	NPC478092
0.8686	High Similarity	NPC473589
0.8659	High Similarity	NPC324144
0.865	High Similarity	NPC119649
0.865	High Similarity	NPC230956
0.865	High Similarity	NPC235143
0.865	High Similarity	NPC271388
0.865	High Similarity	NPC205255
0.8639	High Similarity	NPC173416
0.8639	High Similarity	NPC293093
0.8639	High Similarity	NPC148709
0.8639	High Similarity	NPC476577
0.8606	High Similarity	NPC238530
0.8606	High Similarity	NPC276944
0.8606	High Similarity	NPC232514
0.8598	High Similarity	NPC80759
0.8598	High Similarity	NPC79402
0.8589	High Similarity	NPC221864
0.858	High Similarity	NPC256124
0.8562	High Similarity	NPC76213
0.8562	High Similarity	NPC277669
0.8554	High Similarity	NPC256012
0.8554	High Similarity	NPC250846
0.8554	High Similarity	NPC124657
0.8554	High Similarity	NPC268503
0.8554	High Similarity	NPC317272
0.8554	High Similarity	NPC240841
0.8554	High Similarity	NPC42549
0.8547	High Similarity	NPC475654
0.8545	High Similarity	NPC1229
0.8544	High Similarity	NPC476144
0.8544	High Similarity	NPC106295
0.8544	High Similarity	NPC210437
0.8544	High Similarity	NPC51957
0.8544	High Similarity	NPC16107
0.8538	High Similarity	NPC243454
0.8538	High Similarity	NPC32154
0.8538	High Similarity	NPC475479
0.8537	High Similarity	NPC27410
0.8537	High Similarity	NPC166014
0.8537	High Similarity	NPC18402
0.8528	High Similarity	NPC129603
0.8516	High Similarity	NPC188163
0.8516	High Similarity	NPC474915
0.8516	High Similarity	NPC328750
0.8516	High Similarity	NPC213206
0.8491	Intermediate Similarity	NPC7467
0.8488	Intermediate Similarity	NPC239584
0.8452	Intermediate Similarity	NPC314682
0.8439	Intermediate Similarity	NPC299990
0.8439	Intermediate Similarity	NPC73492
0.8438	Intermediate Similarity	NPC207824
0.8438	Intermediate Similarity	NPC60538
0.8424	Intermediate Similarity	NPC249274
0.8424	Intermediate Similarity	NPC205167
0.8421	Intermediate Similarity	NPC241704
0.8415	Intermediate Similarity	NPC148014
0.8415	Intermediate Similarity	NPC40389
0.8415	Intermediate Similarity	NPC78359
0.8415	Intermediate Similarity	NPC315707
0.8415	Intermediate Similarity	NPC65490
0.8412	Intermediate Similarity	NPC477020
0.8412	Intermediate Similarity	NPC192135
0.8412	Intermediate Similarity	NPC66341

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 NPC83198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	786
0.2-0.3	1138
0.3-0.4	2169
0.4-0.5	2421
0.5-0.6	1535
0.6-0.7	711
0.7-0.8	161
0.8-0.85	11
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9217	High Similarity	NPD8053	Approved
0.9217	High Similarity	NPD8054	Approved
0.8795	High Similarity	NPD8252	Approved
0.8795	High Similarity	NPD8099	Discontinued
0.8795	High Similarity	NPD8251	Approved
0.8743	High Similarity	NPD8156	Discontinued
0.8544	High Similarity	NPD4584	Approved
0.8516	High Similarity	NPD4664	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6071	Discontinued
0.8415	Intermediate Similarity	NPD2560	Approved
0.8415	Intermediate Similarity	NPD2563	Approved
0.8364	Intermediate Similarity	NPD6788	Approved
0.8235	Intermediate Similarity	NPD27	Approved
0.8235	Intermediate Similarity	NPD2489	Approved
0.8232	Intermediate Similarity	NPD4773	Phase 2
0.8232	Intermediate Similarity	NPD4772	Phase 2
0.8199	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD7906	Approved
0.8176	Intermediate Similarity	NPD2969	Approved
0.8176	Intermediate Similarity	NPD2970	Approved
0.8118	Intermediate Similarity	NPD3051	Approved
0.8118	Intermediate Similarity	NPD4010	Discontinued
0.8095	Intermediate Similarity	NPD4055	Discovery
0.8068	Intermediate Similarity	NPD4578	Approved
0.8068	Intermediate Similarity	NPD7310	Approved
0.8068	Intermediate Similarity	NPD7313	Approved
0.8068	Intermediate Similarity	NPD7312	Approved
0.8068	Intermediate Similarity	NPD4577	Approved
0.8068	Intermediate Similarity	NPD7311	Approved
0.8034	Intermediate Similarity	NPD4663	Approved
0.8023	Intermediate Similarity	NPD7309	Approved
0.8023	Intermediate Similarity	NPD2898	Approved
0.8012	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6030	Approved
0.7988	Intermediate Similarity	NPD6031	Approved
0.7975	Intermediate Similarity	NPD1424	Approved
0.7917	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD8095	Phase 1
0.7892	Intermediate Similarity	NPD4017	Approved
0.7892	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7833	Phase 2
0.7882	Intermediate Similarity	NPD7831	Phase 2
0.7862	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD4678	Approved
0.7844	Intermediate Similarity	NPD4675	Approved
0.7805	Intermediate Similarity	NPD2420	Approved
0.7805	Intermediate Similarity	NPD2421	Approved
0.7791	Intermediate Similarity	NPD5677	Discontinued
0.7791	Intermediate Similarity	NPD5241	Discontinued
0.7791	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4005	Discontinued
0.7758	Intermediate Similarity	NPD7447	Phase 1
0.7751	Intermediate Similarity	NPD7298	Approved
0.7744	Intermediate Similarity	NPD7124	Phase 2
0.773	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4481	Phase 3
0.7709	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7549	Discontinued
0.7702	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7212	Phase 2
0.7697	Intermediate Similarity	NPD7213	Phase 3
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5177	Phase 3
0.7665	Intermediate Similarity	NPD3639	Approved
0.7665	Intermediate Similarity	NPD3641	Approved
0.7665	Intermediate Similarity	NPD3640	Phase 3
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3452	Approved
0.7619	Intermediate Similarity	NPD2494	Approved
0.7619	Intermediate Similarity	NPD2493	Approved
0.7619	Intermediate Similarity	NPD3450	Approved
0.7616	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2488	Approved
0.7609	Intermediate Similarity	NPD2490	Approved
0.758	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5005	Approved
0.7579	Intermediate Similarity	NPD5006	Approved
0.7578	Intermediate Similarity	NPD2200	Suspended
0.7547	Intermediate Similarity	NPD4475	Approved
0.7547	Intermediate Similarity	NPD4474	Approved
0.7545	Intermediate Similarity	NPD4123	Phase 3
0.753	Intermediate Similarity	NPD3845	Phase 1
0.7515	Intermediate Similarity	NPD6748	Discontinued
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD4582	Approved
0.75	Intermediate Similarity	NPD4585	Approved
0.75	Intermediate Similarity	NPD4583	Approved
0.75	Intermediate Similarity	NPD6090	Discontinued
0.75	Intermediate Similarity	NPD5772	Approved
0.7485	Intermediate Similarity	NPD5089	Approved
0.7485	Intermediate Similarity	NPD5090	Approved
0.7485	Intermediate Similarity	NPD6072	Discontinued
0.7484	Intermediate Similarity	NPD5718	Phase 2
0.7455	Intermediate Similarity	NPD4236	Phase 3
0.7455	Intermediate Similarity	NPD4237	Approved
0.7455	Intermediate Similarity	NPD4162	Approved
0.7455	Intermediate Similarity	NPD3060	Approved
0.7448	Intermediate Similarity	NPD4002	Approved
0.7448	Intermediate Similarity	NPD4004	Approved
0.7443	Intermediate Similarity	NPD6107	Approved
0.7439	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2674	Phase 3
0.7432	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7407	Intermediate Similarity	NPD2973	Approved
0.7407	Intermediate Similarity	NPD2974	Approved
0.7407	Intermediate Similarity	NPD2975	Approved
0.7403	Intermediate Similarity	NPD6297	Approved
0.7399	Intermediate Similarity	NPD2977	Approved
0.7399	Intermediate Similarity	NPD2978	Approved
0.7391	Intermediate Similarity	NPD2238	Phase 2
0.7382	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4420	Approved
0.7365	Intermediate Similarity	NPD2677	Approved
0.7365	Intermediate Similarity	NPD3692	Discontinued
0.7337	Intermediate Similarity	NPD6853	Approved
0.7337	Intermediate Similarity	NPD6851	Approved
0.7321	Intermediate Similarity	NPD6667	Approved
0.7321	Intermediate Similarity	NPD6666	Approved
0.7317	Intermediate Similarity	NPD1753	Discontinued
0.73	Intermediate Similarity	NPD7047	Phase 3
0.7294	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4580	Approved
0.7288	Intermediate Similarity	NPD4666	Phase 3
0.7283	Intermediate Similarity	NPD2971	Approved
0.7283	Intermediate Similarity	NPD2968	Approved
0.7278	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3144	Approved
0.7267	Intermediate Similarity	NPD3145	Approved
0.7262	Intermediate Similarity	NPD5160	Discontinued
0.7262	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6895	Approved
0.7256	Intermediate Similarity	NPD6111	Discontinued
0.7256	Intermediate Similarity	NPD6896	Approved
0.7255	Intermediate Similarity	NPD6997	Phase 2
0.7251	Intermediate Similarity	NPD5976	Discontinued
0.7251	Intermediate Similarity	NPD2122	Discontinued
0.725	Intermediate Similarity	NPD4908	Phase 1
0.7247	Intermediate Similarity	NPD7802	Discontinued
0.7232	Intermediate Similarity	NPD5709	Phase 3
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6843	Phase 3
0.7219	Intermediate Similarity	NPD6841	Approved
0.7219	Intermediate Similarity	NPD6842	Approved
0.7213	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4625	Phase 3
0.7202	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7466	Approved
0.72	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6042	Phase 2
0.7198	Intermediate Similarity	NPD5312	Approved
0.7198	Intermediate Similarity	NPD5313	Approved
0.7198	Intermediate Similarity	NPD42	Phase 2
0.7198	Intermediate Similarity	NPD4873	Discontinued
0.7184	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7110	Phase 1
0.7176	Intermediate Similarity	NPD3124	Discontinued
0.7168	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5242	Approved
0.716	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7827	Phase 1
0.7143	Intermediate Similarity	NPD3383	Approved
0.7143	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4040	Phase 1
0.7143	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3384	Approved
0.7143	Intermediate Similarity	NPD3382	Approved
0.7135	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7126	Intermediate Similarity	NPD3656	Approved
0.7118	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4166	Phase 2
0.711	Intermediate Similarity	NPD4210	Discontinued
0.7108	Intermediate Similarity	NPD2155	Approved
0.7108	Intermediate Similarity	NPD2154	Approved
0.7108	Intermediate Similarity	NPD2156	Approved
0.7101	Intermediate Similarity	NPD6331	Phase 2
0.7095	Intermediate Similarity	NPD3365	Discontinued
0.7093	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2233	Approved
0.7089	Intermediate Similarity	NPD2232	Approved
0.7089	Intermediate Similarity	NPD2230	Approved
0.7079	Intermediate Similarity	NPD5604	Discontinued
0.7076	Intermediate Similarity	NPD1774	Approved
0.7063	Intermediate Similarity	NPD3053	Approved
0.7063	Intermediate Similarity	NPD4098	Discontinued
0.7063	Intermediate Similarity	NPD3055	Approved
0.7062	Intermediate Similarity	NPD5978	Approved
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5977	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