NPASS Compound

Structure

NPC158900 OpenBabel07101718322D 34 35 0 0 1 0 0 0 0 0999 V2000 13.8564 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 12.1244 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 2 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 6.9282 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 3 33 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 21 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 21 30 2 0 0 0 0 22 2 1 1 0 0 0 22 26 1 0 0 0 0 22 29 1 0 0 0 0 24 13 1 1 0 0 0 24 29 1 0 0 0 0 25 27 2 0 0 0 0 25 31 1 0 0 0 0 26 34 1 1 0 0 0 27 33 1 0 0 0 0 28 32 2 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	473.31
Volume:	514.86
LogP:	5.759
LogD:	4.195
LogS:	-5.666
# Rotatable Bonds:	16
TPSA:	84.86
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.186
Synthetic Accessibility Score:	3.682
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.948
MDCK Permeability:	3.2821295462781563e-05
Pgp-inhibitor:	0.522
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.333
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	97.03314971923828%
Volume Distribution (VD):	1.551
Pgp-substrate:	2.297001361846924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.217
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.641
CYP2C19-substrate:	0.236
CYP2C9-inhibitor:	0.264
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.977
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.688
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	2.127
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.712
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.353
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.959
Carcinogencity:	0.064
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC158900

Natural Product ID:	NPC158900
*Common Name:**	(+)-3-O-Feruloylcassine
IUPAC Name:	[(2R,3R,6S)-2-methyl-6-(11-oxododecyl)piperidin-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	STSLNURRVKPSHZ-VQQILSIJSA-N
Standard InCHI:	InChI=1S/C28H43NO5/c1-21(30)12-10-8-6-4-5-7-9-11-13-24-16-18-26(22(2)29-24)34-28(32)19-15-23-14-17-25(31)27(20-23)33-3/h14-15,17,19-20,22,24,26,29,31H,4-13,16,18H2,1-3H3/p+1/b19-15+/t22-,24+,26-/m1/s1
SMILES:	CC(=O)CCCCCCCCCC[C@H]1CC[C@H]([C@@H](C)[NH2+]1)OC(=O)/C=C/c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249463
PubChem CID:	24763163
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids 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
NPO32445	cassia spectabilis	Species	Fabaceae	Eukaryota	flowers and green fruits	n.a.	n.a.	PMID[15165164]
NPO32445	cassia spectabilis	Species	Fabaceae	Eukaryota	green fruits	n.a.	n.a.	PMID[18047293]

☑ 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
Others	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	33.0	%	PMID[555544]
NPT35	Others	n.a.		deltaA	=	40.0	%	PMID[555544]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[555544]

☑ 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 NPC158900 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	189
0.1-0.2	901
0.2-0.3	3711
0.3-0.4	10950
0.4-0.5	7116
0.5-0.6	9388
0.6-0.7	9680
0.7-0.8	757
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8366	Intermediate Similarity	NPC66518
0.8354	Intermediate Similarity	NPC35345
0.8235	Intermediate Similarity	NPC329816
0.8158	Intermediate Similarity	NPC471110
0.8092	Intermediate Similarity	NPC475468
0.8084	Intermediate Similarity	NPC474858
0.8013	Intermediate Similarity	NPC204546
0.8	Intermediate Similarity	NPC231572
0.7962	Intermediate Similarity	NPC908
0.7962	Intermediate Similarity	NPC138438
0.795	Intermediate Similarity	NPC469539
0.795	Intermediate Similarity	NPC469540
0.7931	Intermediate Similarity	NPC473562
0.7919	Intermediate Similarity	NPC280767
0.787	Intermediate Similarity	NPC329717
0.7852	Intermediate Similarity	NPC20443
0.7852	Intermediate Similarity	NPC273686
0.7852	Intermediate Similarity	NPC146886
0.7852	Intermediate Similarity	NPC312404
0.7852	Intermediate Similarity	NPC60517
0.7843	Intermediate Similarity	NPC88667
0.7834	Intermediate Similarity	NPC284409
0.7821	Intermediate Similarity	NPC90431
0.7815	Intermediate Similarity	NPC151167
0.7815	Intermediate Similarity	NPC5018
0.7815	Intermediate Similarity	NPC276466
0.7815	Intermediate Similarity	NPC123722
0.7815	Intermediate Similarity	NPC123228
0.7785	Intermediate Similarity	NPC242372
0.7785	Intermediate Similarity	NPC4181
0.7785	Intermediate Similarity	NPC289690
0.7785	Intermediate Similarity	NPC257976
0.7785	Intermediate Similarity	NPC164778
0.7785	Intermediate Similarity	NPC288452
0.775	Intermediate Similarity	NPC294249
0.7748	Intermediate Similarity	NPC303680
0.7748	Intermediate Similarity	NPC90128
0.7748	Intermediate Similarity	NPC179777
0.7748	Intermediate Similarity	NPC84076
0.7748	Intermediate Similarity	NPC213552
0.7748	Intermediate Similarity	NPC120225
0.7746	Intermediate Similarity	NPC329992
0.7744	Intermediate Similarity	NPC277669
0.7744	Intermediate Similarity	NPC76213
0.7718	Intermediate Similarity	NPC114298
0.7712	Intermediate Similarity	NPC304622
0.7712	Intermediate Similarity	NPC241354
0.7712	Intermediate Similarity	NPC83062
0.7688	Intermediate Similarity	NPC254053
0.7682	Intermediate Similarity	NPC289459
0.7679	Intermediate Similarity	NPC329640
0.7669	Intermediate Similarity	NPC153644
0.7665	Intermediate Similarity	NPC160931
0.7665	Intermediate Similarity	NPC37205
0.7662	Intermediate Similarity	NPC172673
0.7651	Intermediate Similarity	NPC177291
0.7651	Intermediate Similarity	NPC477564
0.7651	Intermediate Similarity	NPC194416
0.7651	Intermediate Similarity	NPC2295
0.7647	Intermediate Similarity	NPC278308
0.764	Intermediate Similarity	NPC475566
0.7633	Intermediate Similarity	NPC26353
0.7622	Intermediate Similarity	NPC207824
0.7622	Intermediate Similarity	NPC60538
0.7616	Intermediate Similarity	NPC246704
0.7593	Intermediate Similarity	NPC469615
0.7584	Intermediate Similarity	NPC229234
0.7584	Intermediate Similarity	NPC158949
0.7584	Intermediate Similarity	NPC204466
0.7582	Intermediate Similarity	NPC161593
0.7582	Intermediate Similarity	NPC145888
0.7582	Intermediate Similarity	NPC20287
0.7582	Intermediate Similarity	NPC293641
0.7582	Intermediate Similarity	NPC20404
0.7582	Intermediate Similarity	NPC16031
0.7582	Intermediate Similarity	NPC12022
0.758	Intermediate Similarity	NPC176814
0.758	Intermediate Similarity	NPC4982
0.758	Intermediate Similarity	NPC68779
0.758	Intermediate Similarity	NPC5310
0.758	Intermediate Similarity	NPC300776
0.7576	Intermediate Similarity	NPC478242
0.7571	Intermediate Similarity	NPC32154
0.7566	Intermediate Similarity	NPC257589
0.7566	Intermediate Similarity	NPC53305
0.7564	Intermediate Similarity	NPC239302
0.7556	Intermediate Similarity	NPC162694
0.755	Intermediate Similarity	NPC163083
0.755	Intermediate Similarity	NPC140359
0.755	Intermediate Similarity	NPC13020
0.7548	Intermediate Similarity	NPC329595
0.7548	Intermediate Similarity	NPC137427
0.7548	Intermediate Similarity	NPC65935
0.7548	Intermediate Similarity	NPC123196
0.7548	Intermediate Similarity	NPC319282
0.7548	Intermediate Similarity	NPC275724
0.7548	Intermediate Similarity	NPC311419
0.7548	Intermediate Similarity	NPC326599
0.7548	Intermediate Similarity	NPC244246
0.7548	Intermediate Similarity	NPC215941
0.7546	Intermediate Similarity	NPC258671
0.7546	Intermediate Similarity	NPC469683
0.7546	Intermediate Similarity	NPC53884
0.7533	Intermediate Similarity	NPC201777
0.7533	Intermediate Similarity	NPC70752
0.7532	Intermediate Similarity	NPC226661
0.7532	Intermediate Similarity	NPC110313
0.7517	Intermediate Similarity	NPC202474
0.7516	Intermediate Similarity	NPC92207
0.7516	Intermediate Similarity	NPC327410
0.7516	Intermediate Similarity	NPC127937
0.7516	Intermediate Similarity	NPC276014
0.7516	Intermediate Similarity	NPC470441
0.7515	Intermediate Similarity	NPC182119
0.7515	Intermediate Similarity	NPC98009
0.7514	Intermediate Similarity	NPC83019
0.7486	Intermediate Similarity	NPC94499
0.7486	Intermediate Similarity	NPC138083
0.7485	Intermediate Similarity	NPC471073
0.7485	Intermediate Similarity	NPC304956
0.7485	Intermediate Similarity	NPC270811
0.7485	Intermediate Similarity	NPC160378
0.7485	Intermediate Similarity	NPC469978
0.7483	Intermediate Similarity	NPC286573
0.747	Intermediate Similarity	NPC476394
0.747	Intermediate Similarity	NPC98809
0.7468	Intermediate Similarity	NPC135127
0.7459	Intermediate Similarity	NPC204580
0.7459	Intermediate Similarity	NPC124626
0.7458	Intermediate Similarity	NPC241704
0.7455	Intermediate Similarity	NPC428
0.7455	Intermediate Similarity	NPC476571
0.7455	Intermediate Similarity	NPC299090
0.7455	Intermediate Similarity	NPC246587
0.7455	Intermediate Similarity	NPC221383
0.7455	Intermediate Similarity	NPC135538
0.7455	Intermediate Similarity	NPC24233
0.7455	Intermediate Similarity	NPC147390
0.7455	Intermediate Similarity	NPC283081
0.7455	Intermediate Similarity	NPC143892
0.7453	Intermediate Similarity	NPC322021
0.7453	Intermediate Similarity	NPC474784
0.7451	Intermediate Similarity	NPC320242
0.745	Intermediate Similarity	NPC299406
0.7446	Intermediate Similarity	NPC469815
0.7446	Intermediate Similarity	NPC469816
0.744	Intermediate Similarity	NPC56635
0.7438	Intermediate Similarity	NPC126206
0.7438	Intermediate Similarity	NPC299583
0.7436	Intermediate Similarity	NPC66905
0.7434	Intermediate Similarity	NPC160900
0.7434	Intermediate Similarity	NPC18984
0.7434	Intermediate Similarity	NPC106659
0.7434	Intermediate Similarity	NPC229084
0.743	Intermediate Similarity	NPC298339
0.7427	Intermediate Similarity	NPC226428
0.7427	Intermediate Similarity	NPC135006
0.7421	Intermediate Similarity	NPC113295
0.7418	Intermediate Similarity	NPC174122
0.7418	Intermediate Similarity	NPC64140
0.7412	Intermediate Similarity	NPC131532
0.741	Intermediate Similarity	NPC472969
0.741	Intermediate Similarity	NPC1580
0.7407	Intermediate Similarity	NPC100675
0.7405	Intermediate Similarity	NPC155209
0.7405	Intermediate Similarity	NPC168799
0.74	Intermediate Similarity	NPC2058
0.7399	Intermediate Similarity	NPC4138
0.7399	Intermediate Similarity	NPC255607
0.7399	Intermediate Similarity	NPC121275
0.7399	Intermediate Similarity	NPC284183
0.7399	Intermediate Similarity	NPC3375
0.7394	Intermediate Similarity	NPC98356
0.7394	Intermediate Similarity	NPC179825
0.7394	Intermediate Similarity	NPC321505
0.7394	Intermediate Similarity	NPC191376
0.7389	Intermediate Similarity	NPC198388
0.7389	Intermediate Similarity	NPC470392
0.7389	Intermediate Similarity	NPC469480
0.7386	Intermediate Similarity	NPC475215
0.7386	Intermediate Similarity	NPC108434
0.7383	Intermediate Similarity	NPC309434
0.7383	Intermediate Similarity	NPC70744
0.7383	Intermediate Similarity	NPC272471
0.7383	Intermediate Similarity	NPC203124
0.7383	Intermediate Similarity	NPC107588
0.7383	Intermediate Similarity	NPC164706
0.7383	Intermediate Similarity	NPC137537
0.7383	Intermediate Similarity	NPC205502
0.7381	Intermediate Similarity	NPC178048
0.7381	Intermediate Similarity	NPC475454
0.7381	Intermediate Similarity	NPC300329
0.7381	Intermediate Similarity	NPC118033
0.7381	Intermediate Similarity	NPC473680
0.7381	Intermediate Similarity	NPC475311
0.7381	Intermediate Similarity	NPC473579
0.7378	Intermediate Similarity	NPC17760
0.7378	Intermediate Similarity	NPC473090
0.7375	Intermediate Similarity	NPC14600
0.7375	Intermediate Similarity	NPC120852

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 NPC158900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	487
0.2-0.3	1093
0.3-0.4	2110
0.4-0.5	2407
0.5-0.6	1732
0.6-0.7	1008
0.7-0.8	176
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8418	Intermediate Similarity	NPD3455	Phase 2
0.8235	Intermediate Similarity	NPD2239	Approved
0.8235	Intermediate Similarity	NPD2240	Approved
0.8129	Intermediate Similarity	NPD7038	Approved
0.8129	Intermediate Similarity	NPD7039	Approved
0.8092	Intermediate Similarity	NPD6853	Approved
0.8092	Intermediate Similarity	NPD6851	Approved
0.8077	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3687	Approved
0.8012	Intermediate Similarity	NPD3686	Approved
0.7975	Intermediate Similarity	NPD6385	Approved
0.7975	Intermediate Similarity	NPD6386	Approved
0.7974	Intermediate Similarity	NPD555	Phase 2
0.7962	Intermediate Similarity	NPD3060	Approved
0.7937	Intermediate Similarity	NPD3536	Discontinued
0.7879	Intermediate Similarity	NPD2978	Approved
0.7879	Intermediate Similarity	NPD2977	Approved
0.7866	Intermediate Similarity	NPD6677	Suspended
0.7861	Intermediate Similarity	NPD6297	Approved
0.7848	Intermediate Similarity	NPD4162	Approved
0.7843	Intermediate Similarity	NPD259	Phase 1
0.7818	Intermediate Similarity	NPD5355	Approved
0.7818	Intermediate Similarity	NPD5356	Approved
0.7811	Intermediate Similarity	NPD6107	Approved
0.7744	Intermediate Similarity	NPD2649	Approved
0.7744	Intermediate Similarity	NPD2651	Approved
0.7725	Intermediate Similarity	NPD5353	Approved
0.7692	Intermediate Similarity	NPD6315	Phase 2
0.7692	Intermediate Similarity	NPD2653	Approved
0.7677	Intermediate Similarity	NPD825	Approved
0.7677	Intermediate Similarity	NPD826	Approved
0.767	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4666	Phase 3
0.7625	Intermediate Similarity	NPD4237	Approved
0.7625	Intermediate Similarity	NPD4236	Phase 3
0.7613	Intermediate Similarity	NPD3532	Approved
0.7613	Intermediate Similarity	NPD3531	Approved
0.7613	Intermediate Similarity	NPD3530	Approved
0.7607	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5709	Phase 3
0.7586	Intermediate Similarity	NPD2163	Approved
0.7582	Intermediate Similarity	NPD9569	Approved
0.758	Intermediate Similarity	NPD3054	Approved
0.758	Intermediate Similarity	NPD3052	Approved
0.75	Intermediate Similarity	NPD4661	Approved
0.75	Intermediate Similarity	NPD4662	Approved
0.7486	Intermediate Similarity	NPD6620	Discovery
0.7468	Intermediate Similarity	NPD817	Approved
0.7468	Intermediate Similarity	NPD823	Approved
0.7456	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1819	Approved
0.7451	Intermediate Similarity	NPD1818	Approved
0.7451	Intermediate Similarity	NPD1820	Approved
0.7451	Intermediate Similarity	NPD1817	Approved
0.744	Intermediate Similarity	NPD6873	Phase 2
0.744	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1774	Approved
0.7438	Intermediate Similarity	NPD9570	Approved
0.7436	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD597	Approved
0.7436	Intermediate Similarity	NPD601	Approved
0.7436	Intermediate Similarity	NPD598	Approved
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD824	Approved
0.7419	Intermediate Similarity	NPD2614	Approved
0.7403	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3146	Approved
0.7389	Intermediate Similarity	NPD1132	Approved
0.7389	Intermediate Similarity	NPD1136	Approved
0.7389	Intermediate Similarity	NPD1130	Approved
0.7386	Intermediate Similarity	NPD2198	Approved
0.7386	Intermediate Similarity	NPD2199	Approved
0.7386	Intermediate Similarity	NPD196	Phase 1
0.7372	Intermediate Similarity	NPD3167	Approved
0.7372	Intermediate Similarity	NPD3165	Approved
0.7372	Intermediate Similarity	NPD9537	Phase 1
0.7372	Intermediate Similarity	NPD9536	Phase 1
0.7372	Intermediate Similarity	NPD5163	Phase 2
0.7372	Intermediate Similarity	NPD3180	Approved
0.7372	Intermediate Similarity	NPD3166	Approved
0.7372	Intermediate Similarity	NPD3179	Approved
0.7372	Intermediate Similarity	NPD3164	Approved
0.7371	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5314	Approved
0.7358	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7608	Discontinued
0.7346	Intermediate Similarity	NPD7153	Discontinued
0.7342	Intermediate Similarity	NPD3061	Approved
0.7342	Intermediate Similarity	NPD3062	Approved
0.7342	Intermediate Similarity	NPD3059	Approved
0.7342	Intermediate Similarity	NPD3140	Approved
0.7342	Intermediate Similarity	NPD3142	Approved
0.7338	Intermediate Similarity	NPD3055	Approved
0.7338	Intermediate Similarity	NPD3053	Approved
0.7329	Intermediate Similarity	NPD6032	Approved
0.7322	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5241	Discontinued
0.7317	Intermediate Similarity	NPD2677	Approved
0.7314	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3640	Phase 3
0.7305	Intermediate Similarity	NPD3641	Approved
0.7305	Intermediate Similarity	NPD3639	Approved
0.7305	Intermediate Similarity	NPD6030	Approved
0.7305	Intermediate Similarity	NPD6031	Approved
0.729	Intermediate Similarity	NPD257	Approved
0.729	Intermediate Similarity	NPD258	Approved
0.7287	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1423	Approved
0.7273	Intermediate Similarity	NPD3122	Phase 3
0.7273	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2898	Approved
0.7267	Intermediate Similarity	NPD2154	Approved
0.7267	Intermediate Similarity	NPD2155	Approved
0.7267	Intermediate Similarity	NPD2156	Approved
0.7256	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4110	Phase 3
0.7247	Intermediate Similarity	NPD5312	Approved
0.7247	Intermediate Similarity	NPD5313	Approved
0.7246	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD52	Approved
0.7246	Intermediate Similarity	NPD2675	Approved
0.7246	Intermediate Similarity	NPD2676	Approved
0.7246	Intermediate Similarity	NPD7526	Approved
0.7239	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1794	Approved
0.7222	Intermediate Similarity	NPD1538	Phase 1
0.7222	Intermediate Similarity	NPD1537	Approved
0.7222	Intermediate Similarity	NPD1519	Approved
0.7219	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7565	Approved
0.7193	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.7189	Intermediate Similarity	NPD2488	Approved
0.7189	Intermediate Similarity	NPD2490	Approved
0.7186	Intermediate Similarity	NPD6419	Discontinued
0.7182	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9620	Approved
0.7179	Intermediate Similarity	NPD9619	Approved
0.7179	Intermediate Similarity	NPD9621	Approved
0.717	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2674	Phase 3
0.717	Intermediate Similarity	NPD5745	Approved
0.7169	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5311	Approved
0.7161	Intermediate Similarity	NPD5310	Approved
0.716	Intermediate Similarity	NPD4124	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5457	Discontinued
0.7151	Intermediate Similarity	NPD5096	Phase 3
0.7151	Intermediate Similarity	NPD5772	Approved
0.7151	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5773	Approved
0.7151	Intermediate Similarity	NPD3933	Discontinued
0.7151	Intermediate Similarity	NPD5095	Phase 3
0.715	Intermediate Similarity	NPD7999	Approved
0.7143	Intermediate Similarity	NPD2492	Phase 1
0.7134	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD8031	Discontinued
0.712	Intermediate Similarity	NPD2493	Approved
0.712	Intermediate Similarity	NPD2494	Approved
0.7117	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1523	Approved
0.7117	Intermediate Similarity	NPD1522	Approved
0.711	Intermediate Similarity	NPD5978	Approved
0.711	Intermediate Similarity	NPD5977	Approved
0.7107	Intermediate Similarity	NPD7827	Phase 1
0.7107	Intermediate Similarity	NPD1336	Approved
0.7107	Intermediate Similarity	NPD5718	Phase 2
0.7104	Intermediate Similarity	NPD6618	Phase 2
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7131	Phase 3
0.7099	Intermediate Similarity	NPD1536	Approved
0.7097	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5722	Discontinued
0.7093	Intermediate Similarity	NPD7577	Discontinued
0.7091	Intermediate Similarity	NPD5062	Approved
0.7091	Intermediate Similarity	NPD5061	Approved
0.7091	Intermediate Similarity	NPD5177	Phase 3
0.7083	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3656	Approved
0.7068	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4420	Approved
0.7048	Intermediate Similarity	NPD8166	Discontinued
0.7044	Intermediate Similarity	NPD5746	Approved
0.7041	Intermediate Similarity	NPD2186	Approved
0.7037	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4772	Phase 2
0.7035	Intermediate Similarity	NPD7930	Approved
0.7035	Intermediate Similarity	NPD4773	Phase 2
0.7035	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7110	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