NPASS Compound

Structure

NPC476338 OpenBabel07101719132D 26 28 0 0 1 0 0 0 0 0999 V2000 4.3345 0.4003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6596 -0.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3837 4.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 4.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6027 -1.5574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3756 0.2995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8089 1.0795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7138 1.1593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8788 2.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6570 0.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9431 0.2005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8788 1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8912 0.8780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 2.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7138 3.0876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0438 1.1593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1631 1.5515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5262 1.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4821 0.8350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0453 2.2811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4409 0.9357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3837 3.0876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7138 4.0517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1482 -0.9527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 12 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 6 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 13 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 22 2 0 0 0 0 20 21 1 6 0 0 0 20 23 1 0 0 0 0 21 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	374.235
LogP:	2.38
LogD:	2.389
LogS:	-3.809
# Rotatable Bonds:	6
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	4.911
Fsp3:	0.476
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:	-4.495
MDCK Permeability:	1.563103978696745e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.266

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605
Plasma Protein Binding (PPB):	80.07213592529297%
Volume Distribution (VD):	0.973
Pgp-substrate:	12.541526794433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.288
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.75

ADMET: Excretion

Clearance (CL):	10.792
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.186
Human Hepatotoxicity (H-HT):	0.475
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.534
Skin Sensitization:	0.368
Carcinogencity:	0.169
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC476338

Natural Product ID:	NPC476338
*Common Name:**	Kadsurenin C
IUPAC Name:	(1S,5S,6R,7R,8S)-7-(3,4-dimethoxyphenyl)-8-hydroxy-5-methoxy-6-methyl-3-prop-2-enylbicyclo[3.2.1]oct-3-en-2-one
Synonyms:	Kadsurenin C
Standard InCHIKey:	YYEUHNBQISBESB-LOPMHCFQSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-6-7-14-11-21(26-5)12(2)17(18(19(14)22)20(21)23)13-8-9-15(24-3)16(10-13)25-4/h6,8-12,17-18,20,23H,1,7H2,2-5H3/t12-,17+,18-,20+,21-/m1/s1
SMILES:	C=CCC1=C[C@]2(OC)[C@H]([C@@H](C1=O)[C@@H]([C@H]2C)c1ccc(c(c1)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL571615
PubChem CID:	45487142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26326	Ocotea macrophylla	Species	Lauraceae	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	6
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	38700.0	nM	PMID[456292]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	312000.0	nM	PMID[456292]
NPT2	Others	Unspecified		IC50	=	117000.0	nM	PMID[456292]
NPT2	Others	Unspecified		Ratio IC50	=	0.124	n.a.	PMID[456292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2330.0	nM	PMID[456292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54600.0	nM	PMID[456292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	999000.0	nM	PMID[456292]

☑ 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 NPC476338 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	346
0.1-0.2	1267
0.2-0.3	2874
0.3-0.4	6907
0.4-0.5	11184
0.5-0.6	5456
0.6-0.7	10027
0.7-0.8	4511
0.8-0.85	102
0.85-0.9	16
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476359
0.9653	High Similarity	NPC476335
0.9521	High Similarity	NPC476364
0.9329	High Similarity	NPC476340
0.9205	High Similarity	NPC476337
0.891	High Similarity	NPC476277
0.8867	High Similarity	NPC28724
0.8784	High Similarity	NPC476336
0.8716	High Similarity	NPC476362
0.8716	High Similarity	NPC30890
0.8707	High Similarity	NPC239608
0.8707	High Similarity	NPC46161
0.8662	High Similarity	NPC327410
0.8562	High Similarity	NPC327225
0.8562	High Similarity	NPC322021
0.8562	High Similarity	NPC474784
0.8503	High Similarity	NPC51681
0.8487	Intermediate Similarity	NPC12854
0.8481	Intermediate Similarity	NPC476244
0.8431	Intermediate Similarity	NPC178048
0.8431	Intermediate Similarity	NPC62354
0.8421	Intermediate Similarity	NPC474903
0.8387	Intermediate Similarity	NPC25127
0.8377	Intermediate Similarity	NPC151425
0.8367	Intermediate Similarity	NPC325625
0.8345	Intermediate Similarity	NPC244876
0.8333	Intermediate Similarity	NPC15743
0.8322	Intermediate Similarity	NPC339621
0.8322	Intermediate Similarity	NPC233961
0.8322	Intermediate Similarity	NPC195292
0.8322	Intermediate Similarity	NPC280399
0.8322	Intermediate Similarity	NPC142985
0.8301	Intermediate Similarity	NPC472567
0.8291	Intermediate Similarity	NPC475095
0.8291	Intermediate Similarity	NPC179914
0.8291	Intermediate Similarity	NPC472565
0.8269	Intermediate Similarity	NPC287504
0.8267	Intermediate Similarity	NPC472564
0.8264	Intermediate Similarity	NPC469480
0.8255	Intermediate Similarity	NPC476334
0.825	Intermediate Similarity	NPC206815
0.8239	Intermediate Similarity	NPC472961
0.8239	Intermediate Similarity	NPC293641
0.8239	Intermediate Similarity	NPC474936
0.8239	Intermediate Similarity	NPC20287
0.8239	Intermediate Similarity	NPC12022
0.8239	Intermediate Similarity	NPC472962
0.8239	Intermediate Similarity	NPC20404
0.8235	Intermediate Similarity	NPC98009
0.8225	Intermediate Similarity	NPC299855
0.8225	Intermediate Similarity	NPC96194
0.8219	Intermediate Similarity	NPC37065
0.8217	Intermediate Similarity	NPC476363
0.8207	Intermediate Similarity	NPC50763
0.8207	Intermediate Similarity	NPC239302
0.8194	Intermediate Similarity	NPC163002
0.8194	Intermediate Similarity	NPC137427
0.8194	Intermediate Similarity	NPC123196
0.8194	Intermediate Similarity	NPC475379
0.8194	Intermediate Similarity	NPC215941
0.8194	Intermediate Similarity	NPC319282
0.8194	Intermediate Similarity	NPC275724
0.8194	Intermediate Similarity	NPC244246
0.8194	Intermediate Similarity	NPC65935
0.8194	Intermediate Similarity	NPC311419
0.8182	Intermediate Similarity	NPC278308
0.8176	Intermediate Similarity	NPC189704
0.817	Intermediate Similarity	NPC30720
0.8165	Intermediate Similarity	NPC478223
0.8163	Intermediate Similarity	NPC139519
0.8163	Intermediate Similarity	NPC470990
0.8137	Intermediate Similarity	NPC476011
0.8133	Intermediate Similarity	NPC78987
0.8133	Intermediate Similarity	NPC82336
0.8129	Intermediate Similarity	NPC476067
0.8129	Intermediate Similarity	NPC475121
0.8101	Intermediate Similarity	NPC180901
0.8101	Intermediate Similarity	NPC300757
0.8101	Intermediate Similarity	NPC475484
0.8098	Intermediate Similarity	NPC130730
0.8098	Intermediate Similarity	NPC301910
0.8095	Intermediate Similarity	NPC145769
0.8092	Intermediate Similarity	NPC50954
0.8092	Intermediate Similarity	NPC473090
0.8089	Intermediate Similarity	NPC131121
0.8079	Intermediate Similarity	NPC104956
0.8077	Intermediate Similarity	NPC472279
0.8075	Intermediate Similarity	NPC131905
0.8069	Intermediate Similarity	NPC172673
0.8067	Intermediate Similarity	NPC4796
0.8063	Intermediate Similarity	NPC477410
0.8063	Intermediate Similarity	NPC76211
0.8052	Intermediate Similarity	NPC153620
0.8052	Intermediate Similarity	NPC24257
0.8039	Intermediate Similarity	NPC469683
0.8039	Intermediate Similarity	NPC327052
0.8039	Intermediate Similarity	NPC223185
0.8039	Intermediate Similarity	NPC213900
0.8026	Intermediate Similarity	NPC229218
0.8026	Intermediate Similarity	NPC176030
0.8026	Intermediate Similarity	NPC192597
0.8026	Intermediate Similarity	NPC141817
0.8026	Intermediate Similarity	NPC169214
0.8013	Intermediate Similarity	NPC237441
0.8013	Intermediate Similarity	NPC100675
0.8013	Intermediate Similarity	NPC136649
0.8	Intermediate Similarity	NPC21956
0.8	Intermediate Similarity	NPC286919
0.8	Intermediate Similarity	NPC78071
0.8	Intermediate Similarity	NPC268602
0.8	Intermediate Similarity	NPC304622
0.8	Intermediate Similarity	NPC475663
0.8	Intermediate Similarity	NPC1580
0.8	Intermediate Similarity	NPC77598
0.7989	Intermediate Similarity	NPC475299
0.7988	Intermediate Similarity	NPC282551
0.7988	Intermediate Similarity	NPC173292
0.7988	Intermediate Similarity	NPC200726
0.7987	Intermediate Similarity	NPC64230
0.7987	Intermediate Similarity	NPC71638
0.7987	Intermediate Similarity	NPC212697
0.7987	Intermediate Similarity	NPC287495
0.7987	Intermediate Similarity	NPC90431
0.7987	Intermediate Similarity	NPC9370
0.7987	Intermediate Similarity	NPC98356
0.7986	Intermediate Similarity	NPC123722
0.7986	Intermediate Similarity	NPC5018
0.7986	Intermediate Similarity	NPC276466
0.7986	Intermediate Similarity	NPC151167
0.7986	Intermediate Similarity	NPC123228
0.7977	Intermediate Similarity	NPC71385
0.7977	Intermediate Similarity	NPC230670
0.7975	Intermediate Similarity	NPC187491
0.7975	Intermediate Similarity	NPC470340
0.7975	Intermediate Similarity	NPC180944
0.7975	Intermediate Similarity	NPC180388
0.7975	Intermediate Similarity	NPC319200
0.7975	Intermediate Similarity	NPC124038
0.7974	Intermediate Similarity	NPC469615
0.7974	Intermediate Similarity	NPC46880
0.7964	Intermediate Similarity	NPC195972
0.7961	Intermediate Similarity	NPC476842
0.7961	Intermediate Similarity	NPC476840
0.7961	Intermediate Similarity	NPC253722
0.7961	Intermediate Similarity	NPC31751
0.7961	Intermediate Similarity	NPC253481
0.7961	Intermediate Similarity	NPC46180
0.7961	Intermediate Similarity	NPC84273
0.7958	Intermediate Similarity	NPC474691
0.7958	Intermediate Similarity	NPC242372
0.7958	Intermediate Similarity	NPC4181
0.7958	Intermediate Similarity	NPC257976
0.7958	Intermediate Similarity	NPC164778
0.795	Intermediate Similarity	NPC187792
0.795	Intermediate Similarity	NPC469384
0.7947	Intermediate Similarity	NPC470855
0.7947	Intermediate Similarity	NPC203351
0.7947	Intermediate Similarity	NPC147379
0.7945	Intermediate Similarity	NPC477694
0.7945	Intermediate Similarity	NPC477705
0.7939	Intermediate Similarity	NPC177362
0.7937	Intermediate Similarity	NPC469474
0.7935	Intermediate Similarity	NPC143892
0.7935	Intermediate Similarity	NPC221383
0.7935	Intermediate Similarity	NPC299090
0.7935	Intermediate Similarity	NPC283081
0.7933	Intermediate Similarity	NPC166184
0.7931	Intermediate Similarity	NPC112708
0.7927	Intermediate Similarity	NPC180586
0.7925	Intermediate Similarity	NPC305710
0.7922	Intermediate Similarity	NPC207732
0.7922	Intermediate Similarity	NPC275278
0.7919	Intermediate Similarity	NPC89504
0.7919	Intermediate Similarity	NPC152209
0.7919	Intermediate Similarity	NPC95485
0.7919	Intermediate Similarity	NPC88065
0.7917	Intermediate Similarity	NPC303680
0.7917	Intermediate Similarity	NPC179777
0.7917	Intermediate Similarity	NPC107739
0.7917	Intermediate Similarity	NPC90128
0.7917	Intermediate Similarity	NPC84076
0.7911	Intermediate Similarity	NPC256406
0.7911	Intermediate Similarity	NPC267091
0.7911	Intermediate Similarity	NPC302783
0.7911	Intermediate Similarity	NPC46882
0.7911	Intermediate Similarity	NPC473201
0.7911	Intermediate Similarity	NPC132990
0.7908	Intermediate Similarity	NPC474966
0.7908	Intermediate Similarity	NPC11314
0.7902	Intermediate Similarity	NPC312404
0.7902	Intermediate Similarity	NPC273686
0.7901	Intermediate Similarity	NPC218471
0.7901	Intermediate Similarity	NPC161947
0.7901	Intermediate Similarity	NPC239818
0.7901	Intermediate Similarity	NPC155302
0.7898	Intermediate Similarity	NPC142876
0.7898	Intermediate Similarity	NPC69430
0.7898	Intermediate Similarity	NPC195763
0.7898	Intermediate Similarity	NPC40290
0.7898	Intermediate Similarity	NPC147224

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 NPC476338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	842
0.2-0.3	1662
0.3-0.4	2605
0.4-0.5	2075
0.5-0.6	1099
0.6-0.7	499
0.7-0.8	63
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7962	Intermediate Similarity	NPD7028	Phase 2
0.7857	Intermediate Similarity	NPD7685	Pre-registration
0.7716	Intermediate Similarity	NPD3882	Suspended
0.7683	Intermediate Similarity	NPD5494	Approved
0.7671	Intermediate Similarity	NPD5647	Approved
0.764	Intermediate Similarity	NPD1934	Approved
0.7636	Intermediate Similarity	NPD8127	Discontinued
0.7619	Intermediate Similarity	NPD9494	Approved
0.7613	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3620	Phase 2
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7199	Phase 2
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.7485	Intermediate Similarity	NPD2801	Approved
0.7465	Intermediate Similarity	NPD5536	Phase 2
0.7423	Intermediate Similarity	NPD37	Approved
0.7419	Intermediate Similarity	NPD5763	Approved
0.7419	Intermediate Similarity	NPD5762	Approved
0.7407	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD3027	Phase 3
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6273	Approved
0.7353	Intermediate Similarity	NPD7473	Discontinued
0.7342	Intermediate Similarity	NPD6190	Approved
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3817	Phase 2
0.7329	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5735	Approved
0.732	Intermediate Similarity	NPD6355	Discontinued
0.7305	Intermediate Similarity	NPD5283	Phase 1
0.7297	Intermediate Similarity	NPD1876	Approved
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7289	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD5761	Phase 2
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6653	Approved
0.7273	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5978	Approved
0.7229	Intermediate Similarity	NPD5977	Approved
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7202	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1510	Phase 2
0.7179	Intermediate Similarity	NPD2799	Discontinued
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.717	Intermediate Similarity	NPD8166	Discontinued
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7168	Intermediate Similarity	NPD7054	Approved
0.7168	Intermediate Similarity	NPD5844	Phase 1
0.7162	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD2796	Approved
0.7134	Intermediate Similarity	NPD5712	Approved
0.7126	Intermediate Similarity	NPD7472	Approved
0.7118	Intermediate Similarity	NPD1247	Approved
0.711	Intermediate Similarity	NPD3751	Discontinued
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7107	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD919	Approved
0.7097	Intermediate Similarity	NPD3657	Discovery
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7091	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD4624	Approved
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7055	Intermediate Similarity	NPD1512	Approved
0.7051	Intermediate Similarity	NPD1607	Approved
0.7048	Intermediate Similarity	NPD6386	Approved
0.7048	Intermediate Similarity	NPD6385	Approved
0.7047	Intermediate Similarity	NPD3972	Approved
0.7045	Intermediate Similarity	NPD6765	Approved
0.7045	Intermediate Similarity	NPD6764	Approved
0.7044	Intermediate Similarity	NPD1549	Phase 2
0.7044	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD228	Approved
0.7041	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD943	Approved
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7228	Approved
0.7007	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7808	Phase 3
0.6994	Remote Similarity	NPD2533	Approved
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2532	Approved
0.6994	Remote Similarity	NPD2534	Approved
0.6989	Remote Similarity	NPD6797	Phase 2
0.6987	Remote Similarity	NPD447	Suspended
0.6981	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2344	Approved
0.698	Remote Similarity	NPD3092	Approved
0.698	Remote Similarity	NPD3705	Approved
0.6977	Remote Similarity	NPD3787	Discontinued
0.6974	Remote Similarity	NPD2798	Approved
0.6959	Remote Similarity	NPD2932	Approved
0.6959	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1283	Approved
0.6949	Remote Similarity	NPD7251	Discontinued
0.6943	Remote Similarity	NPD6353	Approved
0.6933	Remote Similarity	NPD4357	Discontinued
0.6928	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD2861	Phase 2
0.6923	Remote Similarity	NPD5353	Approved
0.6908	Remote Similarity	NPD3094	Phase 2
0.6903	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6798	Discontinued
0.6894	Remote Similarity	NPD2800	Approved
0.6893	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1357	Approved
0.689	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6785	Approved
0.6889	Remote Similarity	NPD6784	Approved
0.6887	Remote Similarity	NPD5327	Phase 3
0.6871	Remote Similarity	NPD7236	Approved
0.6859	Remote Similarity	NPD6663	Approved
0.6859	Remote Similarity	NPD8032	Phase 2
0.6854	Remote Similarity	NPD6559	Discontinued
0.6854	Remote Similarity	NPD7240	Approved
0.6852	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7157	Approved
0.6846	Remote Similarity	NPD3019	Approved
0.6845	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD8651	Approved
0.6839	Remote Similarity	NPD5242	Approved
0.6839	Remote Similarity	NPD7095	Approved
0.6835	Remote Similarity	NPD6651	Approved
0.6832	Remote Similarity	NPD5958	Discontinued
0.6831	Remote Similarity	NPD2684	Approved
0.6826	Remote Similarity	NPD3226	Approved
0.6824	Remote Similarity	NPD9545	Approved
0.6824	Remote Similarity	NPD5402	Approved
0.6818	Remote Similarity	NPD7799	Discontinued
0.6818	Remote Similarity	NPD5736	Approved
0.6818	Remote Similarity	NPD2163	Approved
0.6815	Remote Similarity	NPD1613	Approved
0.6815	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4060	Phase 1
0.6813	Remote Similarity	NPD6100	Approved
0.6813	Remote Similarity	NPD2438	Suspended
0.6813	Remote Similarity	NPD6099	Approved
0.681	Remote Similarity	NPD2309	Approved
0.6797	Remote Similarity	NPD6362	Approved
0.6795	Remote Similarity	NPD3764	Approved
0.6793	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4237	Approved
0.679	Remote Similarity	NPD4236	Phase 3
0.6789	Remote Similarity	NPD7497	Discontinued
0.6788	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3146	Approved
0.6782	Remote Similarity	NPD7315	Approved
0.678	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2346	Discontinued
0.677	Remote Similarity	NPD7266	Discontinued
0.6765	Remote Similarity	NPD1465	Phase 2
0.6759	Remote Similarity	NPD7843	Approved
0.6758	Remote Similarity	NPD8150	Discontinued
0.6755	Remote Similarity	NPD1281	Approved
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6085	Phase 2
0.6752	Remote Similarity	NPD6233	Phase 2
0.6752	Remote Similarity	NPD4062	Phase 3
0.675	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6331	Phase 2
0.6746	Remote Similarity	NPD6873	Phase 2
0.6733	Remote Similarity	NPD3095	Discontinued
0.6733	Remote Similarity	NPD4626	Approved
0.6724	Remote Similarity	NPD6959	Discontinued
0.6711	Remote Similarity	NPD3091	Approved
0.6709	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2979	Phase 3
0.6708	Remote Similarity	NPD2161	Phase 2
0.6707	Remote Similarity	NPD920	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