NPASS Compound

Structure

CID149090 OpenBabel06191715522D 27 31 0 0 1 0 0 0 0 0999 V2000 -3.9166 -3.4260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5850 2.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1610 2.6618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8034 -1.3904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5015 -2.9559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3057 -3.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9299 -1.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7460 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1305 0.7923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3779 0.8488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9259 -0.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4966 -2.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1181 -0.1476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1205 -2.0211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7584 0.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9507 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3013 -1.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3086 -0.6150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6896 -1.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4952 -0.1572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6905 -0.6217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1104 -2.9548 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5727 1.2267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9630 2.1846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1147 -2.0124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3020 0.7517 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 11 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 7 1 1 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.16
Volume:	368.119
LogP:	2.779
LogD:	2.928
LogS:	-3.057
# Rotatable Bonds:	3
TPSA:	49.39
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.828
Synthetic Accessibility Score:	3.268
Fsp3:	0.429
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:	-4.767
MDCK Permeability:	3.35004115186166e-05
Pgp-inhibitor:	0.48
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	77.59404754638672%
Volume Distribution (VD):	2.015
Pgp-substrate:	12.174214363098145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.323
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.185
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.196
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.604
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	12.141
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.202
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.489
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.79
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.133
Carcinogencity:	0.214
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC149090

Natural Product ID:	NPC149090
*Common Name:**	Ocoteine
IUPAC Name:	n.a.
Synonyms:	Ocoteine
Standard InCHIKey:	XEZKWYLHAOYOCL-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C21H23NO5/c1-22-6-5-12-17-14(22)7-11-8-15(23-2)16(24-3)9-13(11)18(17)20-21(19(12)25-4)27-10-26-20/h8-9,14H,5-7,10H2,1-4H3/p+1/t14-/m0/s1
SMILES:	C[NH+]1CCc2c3[C@@H]1Cc1cc(c(cc1-c3c1c(c2OC)OCO1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443099
PubChem CID:	52499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO7891	Verbena littoralis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11421751]
NPO7891	Verbena littoralis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12762811]
NPO32857	cassytha filiformis ii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677264]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7891	Verbena littoralis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2099	Asteronyx loveni	Species	Asteronychidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7891	Verbena littoralis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO478	Mazzaella laminarioides	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8039	Wikstroemia hainanensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5394	Litsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6146	Stereocaulon sterile	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2533	Cardamine amara	Species	Brassicaceae	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
Others	3

Activity Type	# Activity
Cell Line	1
CELL-LINE	3
Organism	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	74300.0	nM	PMID[518232]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[518231]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	87.7	%	PMID[518231]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	34800.0	nM	PMID[518232]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	51200.0	nM	PMID[518232]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	18.89	ug.mL-1	PMID[518233]
NPT26819	SINGLE PROTEIN	Sclerostin	Homo sapiens	IC50	=	1500.0	nM	PMID[518234]

☑ 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 NPC149090 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	403
0.1-0.2	1860
0.2-0.3	8577
0.3-0.4	9846
0.4-0.5	6196
0.5-0.6	11145
0.6-0.7	3609
0.7-0.8	704
0.8-0.85	219
0.85-0.9	97
0.9-0.95	32
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19520
0.9682	High Similarity	NPC302527
0.9682	High Similarity	NPC16805
0.9682	High Similarity	NPC167546
0.962	High Similarity	NPC24264
0.962	High Similarity	NPC476432
0.9571	High Similarity	NPC470879
0.9571	High Similarity	NPC258695
0.956	High Similarity	NPC247389
0.956	High Similarity	NPC210918
0.9557	High Similarity	NPC225774
0.9512	High Similarity	NPC32413
0.9512	High Similarity	NPC474506
0.9509	High Similarity	NPC23219
0.9497	High Similarity	NPC219341
0.9448	High Similarity	NPC112575
0.9367	High Similarity	NPC160298
0.9367	High Similarity	NPC306902
0.9367	High Similarity	NPC232924
0.9367	High Similarity	NPC477559
0.9367	High Similarity	NPC266753
0.9321	High Similarity	NPC6152
0.929	High Similarity	NPC82763
0.9286	High Similarity	NPC57036
0.9286	High Similarity	NPC214116
0.9268	High Similarity	NPC128560
0.9268	High Similarity	NPC199465
0.9268	High Similarity	NPC229166
0.9236	High Similarity	NPC99659
0.9236	High Similarity	NPC325871
0.9231	High Similarity	NPC186546
0.9231	High Similarity	NPC476576
0.9198	High Similarity	NPC204947
0.9157	High Similarity	NPC320223
0.9157	High Similarity	NPC114364
0.9146	High Similarity	NPC239775
0.9119	High Similarity	NPC476572
0.908	High Similarity	NPC298979
0.9024	High Similarity	NPC241055
0.9018	High Similarity	NPC304659
0.9018	High Similarity	NPC86144
0.8994	High Similarity	NPC116284
0.8994	High Similarity	NPC248642
0.8988	High Similarity	NPC126284
0.897	High Similarity	NPC168753
0.897	High Similarity	NPC118274
0.896	High Similarity	NPC117717
0.8957	High Similarity	NPC168409
0.8941	High Similarity	NPC156576
0.8935	High Similarity	NPC476574
0.8935	High Similarity	NPC312918
0.8935	High Similarity	NPC477561
0.8935	High Similarity	NPC155442
0.8924	High Similarity	NPC326316
0.8924	High Similarity	NPC81733
0.8896	High Similarity	NPC189470
0.8876	High Similarity	NPC267408
0.8841	High Similarity	NPC196447
0.8841	High Similarity	NPC477563
0.8841	High Similarity	NPC78222
0.8841	High Similarity	NPC96603
0.8841	High Similarity	NPC212794
0.8841	High Similarity	NPC306843
0.8841	High Similarity	NPC253043
0.8841	High Similarity	NPC13504
0.8841	High Similarity	NPC136508
0.883	High Similarity	NPC135772
0.8817	High Similarity	NPC148693
0.8817	High Similarity	NPC118633
0.8817	High Similarity	NPC294790
0.881	High Similarity	NPC477558
0.8786	High Similarity	NPC237579
0.878	High Similarity	NPC324144
0.8772	High Similarity	NPC73492
0.8772	High Similarity	NPC299990
0.8765	High Similarity	NPC474507
0.8758	High Similarity	NPC41178
0.8758	High Similarity	NPC138487
0.8758	High Similarity	NPC216459
0.8758	High Similarity	NPC244112
0.8743	High Similarity	NPC75958
0.8735	High Similarity	NPC81218
0.8735	High Similarity	NPC117188
0.8735	High Similarity	NPC205421
0.8735	High Similarity	NPC145832
0.8735	High Similarity	NPC306555
0.8735	High Similarity	NPC474931
0.8735	High Similarity	NPC12053
0.8735	High Similarity	NPC158376
0.8734	High Similarity	NPC475959
0.8734	High Similarity	NPC37144
0.8734	High Similarity	NPC59907
0.8721	High Similarity	NPC302275
0.8704	High Similarity	NPC146288
0.8678	High Similarity	NPC312531
0.8647	High Similarity	NPC148709
0.8647	High Similarity	NPC476577
0.8647	High Similarity	NPC173416
0.8642	High Similarity	NPC123323
0.8634	High Similarity	NPC210148
0.8634	High Similarity	NPC233029
0.8631	High Similarity	NPC152212
0.8621	High Similarity	NPC47077
0.8621	High Similarity	NPC14507
0.8614	High Similarity	NPC180306
0.8598	High Similarity	NPC477080
0.8589	High Similarity	NPC203784
0.8589	High Similarity	NPC170503
0.8589	High Similarity	NPC126519
0.8589	High Similarity	NPC31311
0.8589	High Similarity	NPC234392
0.8562	High Similarity	NPC211296
0.8555	High Similarity	NPC476575
0.8554	High Similarity	NPC1229
0.8545	High Similarity	NPC166014
0.8545	High Similarity	NPC27410
0.8528	High Similarity	NPC76079
0.8523	High Similarity	NPC281581
0.8521	High Similarity	NPC26240
0.8521	High Similarity	NPC69712
0.8521	High Similarity	NPC477562
0.8503	High Similarity	NPC24465
0.85	High Similarity	NPC130941
0.8497	Intermediate Similarity	NPC179704
0.8475	Intermediate Similarity	NPC475754
0.8475	Intermediate Similarity	NPC475597
0.8475	Intermediate Similarity	NPC473716
0.8471	Intermediate Similarity	NPC65403
0.8452	Intermediate Similarity	NPC13916
0.8452	Intermediate Similarity	NPC264850
0.8448	Intermediate Similarity	NPC275132
0.8447	Intermediate Similarity	NPC219162
0.8439	Intermediate Similarity	NPC220961
0.8439	Intermediate Similarity	NPC244554
0.8434	Intermediate Similarity	NPC119649
0.8434	Intermediate Similarity	NPC230956
0.8434	Intermediate Similarity	NPC205255
0.8434	Intermediate Similarity	NPC271388
0.8434	Intermediate Similarity	NPC235143
0.843	Intermediate Similarity	NPC287588
0.8427	Intermediate Similarity	NPC24260
0.8427	Intermediate Similarity	NPC478093
0.8421	Intermediate Similarity	NPC66341
0.8421	Intermediate Similarity	NPC192135
0.8421	Intermediate Similarity	NPC477020
0.8421	Intermediate Similarity	NPC2314
0.8415	Intermediate Similarity	NPC93593
0.8393	Intermediate Similarity	NPC276944
0.8393	Intermediate Similarity	NPC232514
0.8393	Intermediate Similarity	NPC238530
0.8387	Intermediate Similarity	NPC46990
0.8383	Intermediate Similarity	NPC79402
0.8383	Intermediate Similarity	NPC80759
0.838	Intermediate Similarity	NPC478092
0.838	Intermediate Similarity	NPC473589
0.838	Intermediate Similarity	NPC478091
0.838	Intermediate Similarity	NPC30182
0.8373	Intermediate Similarity	NPC111485
0.8373	Intermediate Similarity	NPC221864
0.8373	Intermediate Similarity	NPC7393
0.8372	Intermediate Similarity	NPC187678
0.8363	Intermediate Similarity	NPC227060
0.8363	Intermediate Similarity	NPC76682
0.8363	Intermediate Similarity	NPC317439
0.8363	Intermediate Similarity	NPC10908
0.8363	Intermediate Similarity	NPC198498
0.8363	Intermediate Similarity	NPC317145
0.8363	Intermediate Similarity	NPC63646
0.8363	Intermediate Similarity	NPC115284
0.8363	Intermediate Similarity	NPC276890
0.8352	Intermediate Similarity	NPC9867
0.8343	Intermediate Similarity	NPC249405
0.8343	Intermediate Similarity	NPC68328
0.8324	Intermediate Similarity	NPC302001
0.8323	Intermediate Similarity	NPC51957
0.8323	Intermediate Similarity	NPC106295
0.8323	Intermediate Similarity	NPC16107
0.8323	Intermediate Similarity	NPC253883
0.8323	Intermediate Similarity	NPC95075
0.8323	Intermediate Similarity	NPC210437
0.8323	Intermediate Similarity	NPC476144
0.8323	Intermediate Similarity	NPC90844
0.8314	Intermediate Similarity	NPC12424
0.8314	Intermediate Similarity	NPC41376
0.8314	Intermediate Similarity	NPC251580
0.8314	Intermediate Similarity	NPC129518
0.8313	Intermediate Similarity	NPC145304
0.8302	Intermediate Similarity	NPC136860
0.8302	Intermediate Similarity	NPC476567
0.8302	Intermediate Similarity	NPC128019
0.8294	Intermediate Similarity	NPC57812
0.8294	Intermediate Similarity	NPC474324
0.8294	Intermediate Similarity	NPC150879
0.8291	Intermediate Similarity	NPC474915
0.8291	Intermediate Similarity	NPC328750
0.8291	Intermediate Similarity	NPC213206
0.8291	Intermediate Similarity	NPC188163
0.8291	Intermediate Similarity	NPC470925
0.8276	Intermediate Similarity	NPC190461
0.8274	Intermediate Similarity	NPC60186

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 NPC149090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	809
0.2-0.3	1130
0.3-0.4	2404
0.4-0.5	2545
0.5-0.6	1465
0.6-0.7	442
0.7-0.8	111
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8363	Intermediate Similarity	NPD8251	Approved
0.8363	Intermediate Similarity	NPD8099	Discontinued
0.8363	Intermediate Similarity	NPD8252	Approved
0.8323	Intermediate Similarity	NPD4584	Approved
0.8314	Intermediate Similarity	NPD8156	Discontinued
0.8291	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD6788	Approved
0.814	Intermediate Similarity	NPD4481	Phase 3
0.8129	Intermediate Similarity	NPD3051	Approved
0.8034	Intermediate Similarity	NPD8054	Approved
0.8034	Intermediate Similarity	NPD8053	Approved
0.8025	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD2969	Approved
0.7977	Intermediate Similarity	NPD2970	Approved
0.7901	Intermediate Similarity	NPD7906	Approved
0.7872	Intermediate Similarity	NPD5005	Approved
0.7872	Intermediate Similarity	NPD5006	Approved
0.7829	Intermediate Similarity	NPD2489	Approved
0.7829	Intermediate Similarity	NPD27	Approved
0.7818	Intermediate Similarity	NPD2421	Approved
0.7818	Intermediate Similarity	NPD2420	Approved
0.7798	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4577	Approved
0.7778	Intermediate Similarity	NPD4578	Approved
0.7765	Intermediate Similarity	NPD7298	Approved
0.7758	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD4420	Approved
0.7747	Intermediate Similarity	NPD4663	Approved
0.7697	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4017	Approved
0.7688	Intermediate Similarity	NPD4055	Discovery
0.768	Intermediate Similarity	NPD7310	Approved
0.768	Intermediate Similarity	NPD7313	Approved
0.768	Intermediate Similarity	NPD2968	Approved
0.768	Intermediate Similarity	NPD2971	Approved
0.768	Intermediate Similarity	NPD7311	Approved
0.768	Intermediate Similarity	NPD7312	Approved
0.7665	Intermediate Similarity	NPD1424	Approved
0.7637	Intermediate Similarity	NPD7309	Approved
0.7624	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3640	Phase 3
0.7574	Intermediate Similarity	NPD3641	Approved
0.7574	Intermediate Similarity	NPD3639	Approved
0.7545	Intermediate Similarity	NPD7124	Phase 2
0.7541	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8095	Phase 1
0.7516	Intermediate Similarity	NPD3110	Approved
0.7516	Intermediate Similarity	NPD3109	Approved
0.7514	Intermediate Similarity	NPD6071	Discontinued
0.7514	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD2975	Approved
0.7513	Intermediate Similarity	NPD2974	Approved
0.7513	Intermediate Similarity	NPD2973	Approved
0.7485	Intermediate Similarity	NPD5241	Discontinued
0.7471	Intermediate Similarity	NPD6031	Approved
0.7471	Intermediate Similarity	NPD2563	Approved
0.7471	Intermediate Similarity	NPD4727	Phase 1
0.7471	Intermediate Similarity	NPD2560	Approved
0.7471	Intermediate Similarity	NPD6030	Approved
0.7439	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD2898	Approved
0.7424	Intermediate Similarity	NPD7827	Phase 1
0.7418	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5677	Discontinued
0.7399	Intermediate Similarity	NPD4773	Phase 2
0.7399	Intermediate Similarity	NPD4772	Phase 2
0.7396	Intermediate Similarity	NPD4580	Approved
0.7386	Intermediate Similarity	NPD7831	Phase 2
0.7386	Intermediate Similarity	NPD7833	Phase 2
0.7386	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4005	Discontinued
0.7358	Intermediate Similarity	NPD3450	Approved
0.7358	Intermediate Similarity	NPD2494	Approved
0.7358	Intermediate Similarity	NPD2493	Approved
0.7358	Intermediate Similarity	NPD3452	Approved
0.734	Intermediate Similarity	NPD2490	Approved
0.734	Intermediate Similarity	NPD2488	Approved
0.7321	Intermediate Similarity	NPD5754	Discontinued
0.7318	Intermediate Similarity	NPD4010	Discontinued
0.7314	Intermediate Similarity	NPD4585	Approved
0.7284	Intermediate Similarity	NPD5718	Phase 2
0.7277	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6107	Approved
0.7263	Intermediate Similarity	NPD7802	Discontinued
0.7257	Intermediate Similarity	NPD3384	Approved
0.7257	Intermediate Similarity	NPD3382	Approved
0.7257	Intermediate Similarity	NPD3383	Approved
0.7245	Intermediate Similarity	NPD4582	Approved
0.7245	Intermediate Similarity	NPD4583	Approved
0.7239	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4166	Phase 2
0.7219	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2978	Approved
0.7216	Intermediate Similarity	NPD2977	Approved
0.7194	Intermediate Similarity	NPD4004	Approved
0.7194	Intermediate Similarity	NPD4002	Approved
0.7191	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5604	Discontinued
0.7169	Intermediate Similarity	NPD6111	Discontinued
0.7168	Intermediate Similarity	NPD5976	Discontinued
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7400	Phase 3
0.7136	Intermediate Similarity	NPD4859	Phase 1
0.7135	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3845	Phase 1
0.7134	Intermediate Similarity	NPD4475	Approved
0.7134	Intermediate Similarity	NPD4474	Approved
0.7128	Intermediate Similarity	NPD4107	Approved
0.7122	Intermediate Similarity	NPD3763	Approved
0.7118	Intermediate Similarity	NPD7466	Approved
0.7112	Intermediate Similarity	NPD7281	Phase 3
0.7112	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7280	Phase 3
0.7112	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5089	Approved
0.7102	Intermediate Similarity	NPD5090	Approved
0.7093	Intermediate Similarity	NPD3124	Discontinued
0.7066	Intermediate Similarity	NPD6896	Approved
0.7066	Intermediate Similarity	NPD6895	Approved
0.7066	Intermediate Similarity	NPD2200	Suspended
0.7062	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD5177	Phase 3
0.7059	Intermediate Similarity	NPD7047	Phase 3
0.7055	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6297	Approved
0.7042	Intermediate Similarity	NPD6625	Approved
0.7042	Intermediate Similarity	NPD6723	Discontinued
0.7027	Intermediate Similarity	NPD5312	Approved
0.7027	Intermediate Similarity	NPD5313	Approved
0.7024	Intermediate Similarity	NPD4108	Discontinued
0.7019	Intermediate Similarity	NPD6997	Phase 2
0.7006	Intermediate Similarity	NPD2492	Phase 1
0.7005	Intermediate Similarity	NPD4482	Phase 3
0.6995	Remote Similarity	NPD5242	Approved
0.6995	Remote Similarity	NPD6688	Approved
0.6995	Remote Similarity	NPD6687	Approved
0.6994	Remote Similarity	NPD5297	Approved
0.6994	Remote Similarity	NPD7598	Phase 2
0.6983	Remote Similarity	NPD5977	Approved
0.6983	Remote Similarity	NPD5978	Approved
0.6963	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4236	Phase 3
0.6959	Remote Similarity	NPD4237	Approved
0.6954	Remote Similarity	NPD7447	Phase 1
0.6954	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4675	Approved
0.6949	Remote Similarity	NPD4678	Approved
0.6944	Remote Similarity	NPD4966	Approved
0.6944	Remote Similarity	NPD4965	Approved
0.6944	Remote Similarity	NPD4967	Phase 2
0.6937	Remote Similarity	NPD3705	Approved
0.6923	Remote Similarity	NPD5582	Discontinued
0.6923	Remote Similarity	NPD6037	Discontinued
0.6919	Remote Similarity	NPD6748	Discontinued
0.6912	Remote Similarity	NPD3815	Phase 1
0.6912	Remote Similarity	NPD3816	Phase 1
0.6897	Remote Similarity	NPD7213	Phase 3
0.6897	Remote Similarity	NPD7212	Phase 2
0.6895	Remote Similarity	NPD6851	Approved
0.6895	Remote Similarity	NPD6853	Approved
0.6884	Remote Similarity	NPD3057	Approved
0.6875	Remote Similarity	NPD3349	Phase 2
0.6875	Remote Similarity	NPD6842	Approved
0.6875	Remote Similarity	NPD6841	Approved
0.6875	Remote Similarity	NPD6843	Phase 3
0.6872	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6234	Discontinued
0.6867	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD8153	Approved
0.6861	Remote Similarity	NPD8152	Approved
0.686	Remote Similarity	NPD6674	Discontinued
0.6839	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4210	Discontinued
0.6818	Remote Similarity	NPD6090	Discontinued
0.6816	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7110	Phase 1
0.6816	Remote Similarity	NPD4040	Phase 1
0.6809	Remote Similarity	NPD3885	Approved
0.6807	Remote Similarity	NPD5155	Approved
0.6807	Remote Similarity	NPD5156	Approved
0.6805	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3533	Approved
0.68	Remote Similarity	NPD2972	Approved
0.6798	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7228	Approved
0.6788	Remote Similarity	NPD7291	Discontinued
0.6784	Remote Similarity	NPD5457	Discontinued
0.678	Remote Similarity	NPD1914	Approved
0.6769	Remote Similarity	NPD7296	Approved
0.6763	Remote Similarity	NPD3060	Approved
0.6757	Remote Similarity	NPD6747	Phase 1

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