NPASS Compound

Structure

NPC60295 OpenBabel07101719152D 41 48 0 0 1 0 0 0 0 0999 V2000 2.3821 -4.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0805 -2.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7880 -2.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6463 -2.4497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2094 -4.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 -2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4142 -3.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9449 -3.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3515 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 -1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5215 -0.2145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 -2.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4199 -1.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1804 -3.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0116 -4.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0605 -1.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 -1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 -1.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6601 -3.8891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4988 -0.7640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9772 -3.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 -1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9860 -0.5088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5161 -2.7830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0072 -3.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6948 -4.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 0.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 -0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4087 -1.2074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3936 -0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0341 -0.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7067 0.0566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8387 -0.2275 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -3.2830 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2763 -2.5707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 -2.0795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3826 -4.0641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9551 -0.6009 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 36 1 0 0 0 0 2 38 1 0 0 0 0 3 6 1 0 0 0 0 3 19 2 0 0 0 0 4 7 2 0 0 0 0 4 19 1 0 0 0 0 5 8 2 0 0 0 0 5 20 1 0 0 0 0 6 23 2 0 0 0 0 7 23 1 0 0 0 0 8 27 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 35 1 0 0 0 0 12 36 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 2 0 0 0 0 15 28 1 0 0 0 0 16 21 2 0 0 0 0 16 29 1 0 0 0 0 17 22 2 0 0 0 0 17 31 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 21 24 1 0 0 0 0 22 32 1 0 0 0 0 23 39 1 0 0 0 0 24 26 1 0 0 0 0 25 13 1 6 0 0 0 25 32 1 0 0 0 0 25 35 1 0 0 0 0 26 14 1 1 0 0 0 26 36 1 0 0 0 0 27 28 2 0 0 0 0 27 37 1 0 0 0 0 28 39 1 0 0 0 0 29 30 2 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 33 2 0 0 0 0 31 38 1 0 0 0 0 32 34 2 0 0 0 0 33 34 1 0 0 0 0 33 40 1 0 0 0 0 34 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	706.43
Volume:	738.304
LogP:	5.831
LogD:	4.83
LogS:	-5.134
# Rotatable Bonds:	20
TPSA:	151.73
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	5.429
Fsp3:	0.821
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.779
MDCK Permeability:	6.305240822257474e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.808
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	89.86885833740234%
Volume Distribution (VD):	0.714
Pgp-substrate:	2.6347861289978027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.703
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.854
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	10.749
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.248
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.253
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.353

Download Data

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

Natural Product: NPC60295

Natural Product ID:	NPC60295
*Common Name:**	AVICOTFUCGWABJ-UIOOFZCWSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-2'-Norcocsuline
Standard InCHIKey:	AVICOTFUCGWABJ-UIOOFZCWSA-N
Standard InCHI:	InChI=1S/C34H32N2O5/c1-36-12-10-21-16-29-30-18-24(21)26(36)14-20-5-8-27(37)28(15-20)39-23-6-3-19(4-7-23)13-25-32-22(9-11-35-25)17-31(38-2)33(40-29)34(32)41-30/h3-8,15-18,25-26,35,37H,9-14H2,1-2H3/t25-,26-/m0/s1
SMILES:	COc1cc2CCN[C@@H]3c2c2c1Oc1cc4CCN([C@H](c4cc1O2)Cc1ccc(c(Oc2ccc(C3)cc2)c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443331
PubChem CID:	44559018
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	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
ED50	1
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3800.0	nM	PMID[572917]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	48.0	nM	PMID[572917]
NPT2	Others	Unspecified		Selectivity Index	=	79.0	n.a.	PMID[572917]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	281.0	nM	PMID[572917]
NPT2	Others	Unspecified		Selectivity Index	=	14.0	n.a.	PMID[572917]

☑ 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 NPC60295 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	373
0.1-0.2	1900
0.2-0.3	9591
0.3-0.4	8630
0.4-0.5	6149
0.5-0.6	9641
0.6-0.7	5278
0.7-0.8	841
0.8-0.85	159
0.85-0.9	48
0.9-0.95	44
0.95-1	43

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191132
0.9941	High Similarity	NPC11296
0.9941	High Similarity	NPC274661
0.9941	High Similarity	NPC82457
0.9941	High Similarity	NPC48490
0.9941	High Similarity	NPC175890
0.9706	High Similarity	NPC167116
0.9706	High Similarity	NPC274716
0.9706	High Similarity	NPC254441
0.9655	High Similarity	NPC256124
0.9647	High Similarity	NPC290582
0.9647	High Similarity	NPC54654
0.9647	High Similarity	NPC181796
0.9647	High Similarity	NPC279228
0.9647	High Similarity	NPC311973
0.9647	High Similarity	NPC8836
0.9647	High Similarity	NPC258657
0.9647	High Similarity	NPC7715
0.9647	High Similarity	NPC229373
0.9647	High Similarity	NPC251735
0.9647	High Similarity	NPC182052
0.9647	High Similarity	NPC239824
0.9647	High Similarity	NPC290005
0.9647	High Similarity	NPC104196
0.9647	High Similarity	NPC285931
0.9647	High Similarity	NPC222661
0.9647	High Similarity	NPC223690
0.9647	High Similarity	NPC217748
0.9647	High Similarity	NPC49075
0.9647	High Similarity	NPC90998
0.9647	High Similarity	NPC42663
0.9647	High Similarity	NPC328155
0.9647	High Similarity	NPC185639
0.9647	High Similarity	NPC15414
0.9647	High Similarity	NPC271013
0.9588	High Similarity	NPC239584
0.9588	High Similarity	NPC286119
0.9532	High Similarity	NPC30779
0.9529	High Similarity	NPC243454
0.9529	High Similarity	NPC475479
0.948	High Similarity	NPC116465
0.948	High Similarity	NPC212237
0.9425	High Similarity	NPC22115
0.9425	High Similarity	NPC275680
0.9371	High Similarity	NPC206900
0.9368	High Similarity	NPC139783
0.9368	High Similarity	NPC65312
0.931	High Similarity	NPC302245
0.931	High Similarity	NPC95426
0.931	High Similarity	NPC16357
0.9294	High Similarity	NPC12424
0.9294	High Similarity	NPC251580
0.9294	High Similarity	NPC129518
0.9294	High Similarity	NPC41376
0.9266	High Similarity	NPC24260
0.9235	High Similarity	NPC475215
0.9235	High Similarity	NPC227060
0.9235	High Similarity	NPC317439
0.9235	High Similarity	NPC115284
0.9235	High Similarity	NPC63646
0.9235	High Similarity	NPC10908
0.9235	High Similarity	NPC317145
0.9235	High Similarity	NPC198498
0.9235	High Similarity	NPC108434
0.9235	High Similarity	NPC76682
0.9235	High Similarity	NPC276890
0.9157	High Similarity	NPC478093
0.9153	High Similarity	NPC281581
0.9106	High Similarity	NPC473589
0.9106	High Similarity	NPC30182
0.9106	High Similarity	NPC478092
0.9106	High Similarity	NPC478091
0.9075	High Similarity	NPC293093
0.9	High Similarity	NPC240841
0.9	High Similarity	NPC268503
0.9	High Similarity	NPC317272
0.9	High Similarity	NPC85381
0.9	High Similarity	NPC256012
0.9	High Similarity	NPC13916
0.9	High Similarity	NPC250846
0.9	High Similarity	NPC264850
0.9	High Similarity	NPC42549
0.8994	High Similarity	NPC318805
0.8994	High Similarity	NPC41122
0.8962	High Similarity	NPC475654
0.8941	High Similarity	NPC24465
0.8901	High Similarity	NPC234318
0.8895	High Similarity	NPC204908
0.8895	High Similarity	NPC83198
0.8882	High Similarity	NPC475393
0.887	High Similarity	NPC73492
0.887	High Similarity	NPC299990
0.8757	High Similarity	NPC474507
0.8743	High Similarity	NPC152680
0.8743	High Similarity	NPC190783
0.8743	High Similarity	NPC232386
0.8736	High Similarity	NPC109925
0.8721	High Similarity	NPC284183
0.8721	High Similarity	NPC4138
0.8721	High Similarity	NPC121275
0.8717	High Similarity	NPC254581
0.8715	High Similarity	NPC302275
0.8708	High Similarity	NPC230276
0.8708	High Similarity	NPC257269
0.8667	High Similarity	NPC249996
0.8652	High Similarity	NPC119068
0.8652	High Similarity	NPC40496
0.8644	High Similarity	NPC148709
0.8644	High Similarity	NPC476577
0.8644	High Similarity	NPC173416
0.8603	High Similarity	NPC195538
0.8588	High Similarity	NPC247639
0.8588	High Similarity	NPC25084
0.8579	High Similarity	NPC473716
0.8579	High Similarity	NPC475597
0.8556	High Similarity	NPC476202
0.8529	High Similarity	NPC39701
0.8529	High Similarity	NPC207757
0.8529	High Similarity	NPC172765
0.8529	High Similarity	NPC184026
0.8529	High Similarity	NPC189266
0.8529	High Similarity	NPC295691
0.8529	High Similarity	NPC5238
0.8529	High Similarity	NPC193949
0.8529	High Similarity	NPC276588
0.8529	High Similarity	NPC2413
0.8529	High Similarity	NPC278799
0.8529	High Similarity	NPC127674
0.8529	High Similarity	NPC204828
0.8529	High Similarity	NPC110416
0.8529	High Similarity	NPC249797
0.8529	High Similarity	NPC469817
0.8529	High Similarity	NPC54379
0.8516	High Similarity	NPC14507
0.8516	High Similarity	NPC47077
0.8475	Intermediate Similarity	NPC239775
0.8471	Intermediate Similarity	NPC2295
0.8471	Intermediate Similarity	NPC477564
0.8457	Intermediate Similarity	NPC223077
0.8457	Intermediate Similarity	NPC56887
0.8457	Intermediate Similarity	NPC193853
0.8427	Intermediate Similarity	NPC66341
0.8427	Intermediate Similarity	NPC192135
0.8427	Intermediate Similarity	NPC477020
0.8418	Intermediate Similarity	NPC477562
0.8418	Intermediate Similarity	NPC168753
0.8418	Intermediate Similarity	NPC69712
0.8418	Intermediate Similarity	NPC118274
0.8418	Intermediate Similarity	NPC26240
0.84	Intermediate Similarity	NPC209377
0.8371	Intermediate Similarity	NPC10871
0.837	Intermediate Similarity	NPC476576
0.837	Intermediate Similarity	NPC186546
0.8353	Intermediate Similarity	NPC277669
0.8353	Intermediate Similarity	NPC76213
0.8314	Intermediate Similarity	NPC187022
0.8314	Intermediate Similarity	NPC80129
0.8305	Intermediate Similarity	NPC204947
0.8294	Intermediate Similarity	NPC88249
0.8294	Intermediate Similarity	NPC192768
0.8294	Intermediate Similarity	NPC97221
0.8294	Intermediate Similarity	NPC151895
0.8294	Intermediate Similarity	NPC220858
0.8286	Intermediate Similarity	NPC60186
0.8249	Intermediate Similarity	NPC476573
0.8249	Intermediate Similarity	NPC35627
0.8249	Intermediate Similarity	NPC81247
0.8241	Intermediate Similarity	NPC82056
0.8235	Intermediate Similarity	NPC207824
0.8235	Intermediate Similarity	NPC476565
0.8235	Intermediate Similarity	NPC103379
0.8235	Intermediate Similarity	NPC477565
0.8235	Intermediate Similarity	NPC60538
0.8232	Intermediate Similarity	NPC38964
0.8229	Intermediate Similarity	NPC235143
0.8229	Intermediate Similarity	NPC119649
0.8229	Intermediate Similarity	NPC271388
0.8229	Intermediate Similarity	NPC205255
0.8229	Intermediate Similarity	NPC230956
0.8216	Intermediate Similarity	NPC57036
0.8202	Intermediate Similarity	NPC474931
0.8202	Intermediate Similarity	NPC81218
0.8202	Intermediate Similarity	NPC158376
0.8202	Intermediate Similarity	NPC117188
0.8202	Intermediate Similarity	NPC205421
0.8202	Intermediate Similarity	NPC306555
0.8202	Intermediate Similarity	NPC145832
0.8202	Intermediate Similarity	NPC12053
0.8192	Intermediate Similarity	NPC212794
0.8192	Intermediate Similarity	NPC253043
0.8192	Intermediate Similarity	NPC276944
0.8192	Intermediate Similarity	NPC238530
0.8192	Intermediate Similarity	NPC13504
0.8192	Intermediate Similarity	NPC96603
0.8192	Intermediate Similarity	NPC232514
0.8192	Intermediate Similarity	NPC136508
0.8192	Intermediate Similarity	NPC477563
0.8192	Intermediate Similarity	NPC306843
0.8192	Intermediate Similarity	NPC78222
0.8192	Intermediate Similarity	NPC196447

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 NPC60295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	749
0.2-0.3	1199
0.3-0.4	2143
0.4-0.5	2534
0.5-0.6	1551
0.6-0.7	650
0.7-0.8	116
0.8-0.85	5
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9647	High Similarity	NPD8053	Approved
0.9647	High Similarity	NPD8054	Approved
0.9235	High Similarity	NPD8251	Approved
0.9235	High Similarity	NPD8099	Discontinued
0.9235	High Similarity	NPD8252	Approved
0.9181	High Similarity	NPD8156	Discontinued
0.8652	High Similarity	NPD8453	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7298	Approved
0.8307	Intermediate Similarity	NPD8095	Phase 1
0.8118	Intermediate Similarity	NPD4584	Approved
0.8068	Intermediate Similarity	NPD6788	Approved
0.7926	Intermediate Similarity	NPD7906	Approved
0.7907	Intermediate Similarity	NPD1424	Approved
0.7841	Intermediate Similarity	NPD4773	Phase 2
0.7841	Intermediate Similarity	NPD4772	Phase 2
0.7816	Intermediate Similarity	NPD6030	Approved
0.7816	Intermediate Similarity	NPD6031	Approved
0.7772	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD6071	Discontinued
0.7722	Intermediate Similarity	NPD7831	Phase 2
0.7722	Intermediate Similarity	NPD7833	Phase 2
0.7722	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD7312	Approved
0.7713	Intermediate Similarity	NPD7313	Approved
0.7713	Intermediate Similarity	NPD7310	Approved
0.7713	Intermediate Similarity	NPD7311	Approved
0.7688	Intermediate Similarity	NPD3845	Phase 1
0.7672	Intermediate Similarity	NPD7309	Approved
0.7667	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD27	Approved
0.7663	Intermediate Similarity	NPD2489	Approved
0.765	Intermediate Similarity	NPD3051	Approved
0.7627	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4577	Approved
0.7619	Intermediate Similarity	NPD4578	Approved
0.7609	Intermediate Similarity	NPD2969	Approved
0.7609	Intermediate Similarity	NPD2970	Approved
0.76	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7447	Phase 1
0.7596	Intermediate Similarity	NPD6107	Approved
0.7592	Intermediate Similarity	NPD4663	Approved
0.7544	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7598	Phase 2
0.7541	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD8152	Approved
0.7523	Intermediate Similarity	NPD8153	Approved
0.7514	Intermediate Similarity	NPD2563	Approved
0.7514	Intermediate Similarity	NPD2560	Approved
0.7486	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7549	Discontinued
0.7459	Intermediate Similarity	NPD4010	Discontinued
0.7457	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7213	Phase 3
0.7443	Intermediate Similarity	NPD7212	Phase 2
0.7396	Intermediate Similarity	NPD6851	Approved
0.7396	Intermediate Similarity	NPD6853	Approved
0.7384	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD2898	Approved
0.7379	Intermediate Similarity	NPD7827	Phase 1
0.7368	Intermediate Similarity	NPD6297	Approved
0.7354	Intermediate Similarity	NPD6042	Phase 2
0.7354	Intermediate Similarity	NPD42	Phase 2
0.7345	Intermediate Similarity	NPD2420	Approved
0.7345	Intermediate Similarity	NPD2421	Approved
0.7337	Intermediate Similarity	NPD4055	Discovery
0.733	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4162	Approved
0.7314	Intermediate Similarity	NPD3060	Approved
0.73	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4678	Approved
0.7293	Intermediate Similarity	NPD4675	Approved
0.7288	Intermediate Similarity	NPD7124	Phase 2
0.7268	Intermediate Similarity	NPD2977	Approved
0.7268	Intermediate Similarity	NPD4585	Approved
0.7268	Intermediate Similarity	NPD2978	Approved
0.7258	Intermediate Similarity	NPD5677	Discontinued
0.7253	Intermediate Similarity	NPD6072	Discontinued
0.7238	Intermediate Similarity	NPD4017	Approved
0.7232	Intermediate Similarity	NPD5241	Discontinued
0.7232	Intermediate Similarity	NPD2677	Approved
0.7232	Intermediate Similarity	NPD5160	Discontinued
0.7228	Intermediate Similarity	NPD3450	Approved
0.7228	Intermediate Similarity	NPD2493	Approved
0.7228	Intermediate Similarity	NPD3452	Approved
0.7228	Intermediate Similarity	NPD2494	Approved
0.7225	Intermediate Similarity	NPD7479	Phase 2
0.7222	Intermediate Similarity	NPD3640	Phase 3
0.7222	Intermediate Similarity	NPD3641	Approved
0.7222	Intermediate Similarity	NPD3639	Approved
0.7219	Intermediate Similarity	NPD7802	Discontinued
0.7208	Intermediate Similarity	NPD2490	Approved
0.7208	Intermediate Similarity	NPD2488	Approved
0.7207	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4481	Phase 3
0.7181	Intermediate Similarity	NPD4166	Phase 2
0.7174	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4873	Discontinued
0.7167	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4666	Phase 3
0.715	Intermediate Similarity	NPD6997	Phase 2
0.7143	Intermediate Similarity	NPD4005	Discontinued
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2122	Discontinued
0.7127	Intermediate Similarity	NPD5976	Discontinued
0.7122	Intermediate Similarity	NPD4582	Approved
0.7122	Intermediate Similarity	NPD4040	Phase 1
0.7122	Intermediate Similarity	NPD4583	Approved
0.712	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5709	Phase 3
0.7109	Intermediate Similarity	NPD7047	Phase 3
0.7093	Intermediate Similarity	NPD4474	Approved
0.7093	Intermediate Similarity	NPD4475	Approved
0.7091	Intermediate Similarity	NPD6723	Discontinued
0.7081	Intermediate Similarity	NPD5773	Approved
0.7081	Intermediate Similarity	NPD5772	Approved
0.7079	Intermediate Similarity	NPD6748	Discontinued
0.7073	Intermediate Similarity	NPD4002	Approved
0.7073	Intermediate Similarity	NPD4004	Approved
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1774	Approved
0.7056	Intermediate Similarity	NPD3124	Discontinued
0.7049	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6618	Phase 2
0.7035	Intermediate Similarity	NPD5718	Phase 2
0.703	Intermediate Similarity	NPD2973	Approved
0.703	Intermediate Similarity	NPD2975	Approved
0.703	Intermediate Similarity	NPD2974	Approved
0.7029	Intermediate Similarity	NPD2200	Suspended
0.7027	Intermediate Similarity	NPD3382	Approved
0.7027	Intermediate Similarity	NPD3383	Approved
0.7027	Intermediate Similarity	NPD3384	Approved
0.7027	Intermediate Similarity	NPD5722	Discontinued
0.7024	Intermediate Similarity	NPD5005	Approved
0.7024	Intermediate Similarity	NPD5006	Approved
0.7022	Intermediate Similarity	NPD5177	Phase 3
0.7018	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4123	Phase 3
0.701	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5313	Approved
0.6995	Remote Similarity	NPD5312	Approved
0.6989	Remote Similarity	NPD2154	Approved
0.6989	Remote Similarity	NPD2155	Approved
0.6989	Remote Similarity	NPD2156	Approved
0.6983	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7466	Approved
0.6978	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7526	Approved
0.6978	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD52	Approved
0.6978	Remote Similarity	NPD6090	Discontinued
0.6966	Remote Similarity	NPD7153	Discontinued
0.6961	Remote Similarity	NPD6087	Phase 1
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1613	Approved
0.6954	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3053	Approved
0.6941	Remote Similarity	NPD3055	Approved
0.6939	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5720	Discontinued
0.6927	Remote Similarity	NPD5061	Approved
0.6927	Remote Similarity	NPD4580	Approved
0.6927	Remote Similarity	NPD5062	Approved
0.6919	Remote Similarity	NPD4908	Phase 1
0.6906	Remote Similarity	NPD3122	Phase 3
0.6904	Remote Similarity	NPD2971	Approved
0.6904	Remote Similarity	NPD2968	Approved
0.6904	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3687	Approved
0.6902	Remote Similarity	NPD3686	Approved
0.69	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.69	Remote Similarity	NPD2845	Phase 2
0.69	Remote Similarity	NPD2843	Phase 2
0.6891	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7039	Approved
0.6888	Remote Similarity	NPD7038	Approved
0.6882	Remote Similarity	NPD5311	Approved
0.6882	Remote Similarity	NPD5310	Approved
0.6875	Remote Similarity	NPD2568	Approved
0.6875	Remote Similarity	NPD817	Approved
0.6875	Remote Similarity	NPD3052	Approved
0.6875	Remote Similarity	NPD823	Approved
0.6875	Remote Similarity	NPD5314	Approved
0.6875	Remote Similarity	NPD3054	Approved
0.6866	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4605	Approved
0.6863	Remote Similarity	NPD4604	Approved
0.6856	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8318	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