NPASS Compound

Structure

NPC476340 OpenBabel07101718312D 30 32 0 0 1 0 0 0 0 0999 V2000 3.1612 -2.1427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5035 -2.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4015 2.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0792 0.0903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2403 2.5119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7693 -3.1233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2670 1.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5552 -1.2578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9858 -0.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7238 1.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5626 -0.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8239 -1.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7836 -1.3573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0592 -0.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7238 0.0903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5626 1.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4015 0.0903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8849 -0.3940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4015 1.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6925 -0.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6481 -0.7198 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1638 -1.5587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2140 0.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6115 -0.6186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5626 2.5119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2403 -0.3940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2403 1.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0149 -2.5158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3447 0.9052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 1 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 23 1 6 0 0 0 19 28 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 22 1 6 0 0 0 21 23 1 0 0 0 0 21 25 1 0 0 0 0 22 29 1 6 0 0 0 23 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.2
Volume:	426.408
LogP:	2.518
LogD:	2.269
LogS:	-4.1
# Rotatable Bonds:	8
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	5.205
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.635
MDCK Permeability:	1.5087341125763487e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.384

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.689
Plasma Protein Binding (PPB):	69.38985443115234%
Volume Distribution (VD):	1.305
Pgp-substrate:	21.311382293701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.234
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.826
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.807

ADMET: Excretion

Clearance (CL):	7.019
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.207
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.478
Skin Sensitization:	0.346
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC476340

Natural Product ID:	NPC476340
*Common Name:**	Nectamazin B
IUPAC Name:	(1S,5R,6R,7S,8R)-8-hydroxy-1,5-dimethoxy-7-methyl-3-prop-2-enyl-6-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-2-en-4-one
Synonyms:
Standard InCHIKey:	IKLPDXKPWBONDW-GAGXKEPLSA-N
Standard InCHI:	InChI=1S/C23H30O7/c1-8-9-14-12-22(29-6)13(2)18(23(30-7,20(14)24)21(22)25)15-10-16(26-3)19(28-5)17(11-15)27-4/h8,10-13,18,21,25H,1,9H2,2-7H3/t13-,18+,21+,22+,23-/m0/s1
SMILES:	CO[C@@]12C(=O)C(=C[C@]([C@H]1O)([C@H]([C@@H]2c1cc(OC)c(c(c1)OC)OC)C)OC)CC=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL571892
PubChem CID:	45487121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
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]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	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	12
Others	2

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	6
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	72200.0	nM	PMID[495859]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	152000.0	nM	PMID[495860]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	255000.0	nM	PMID[495859]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	569000.0	nM	PMID[495860]
NPT2	Others	Unspecified		IC50	=	156000.0	nM	PMID[495859]
NPT2	Others	Unspecified		IC50	=	42400.0	nM	PMID[495860]
NPT2	Others	Unspecified		Ratio IC50	=	0.283	n.a.	PMID[495859]
NPT2	Others	Unspecified		Ratio IC50	=	0.266	n.a.	PMID[495860]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1370.0	nM	PMID[495859]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1720.0	nM	PMID[495860]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	68700.0	nM	PMID[495859]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43400.0	nM	PMID[495860]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	999000.0	nM	PMID[495859]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	999000.0	nM	PMID[495860]

☑ 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 NPC476340 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	394
0.1-0.2	1351
0.2-0.3	3167
0.3-0.4	7517
0.4-0.5	10545
0.5-0.6	5822
0.6-0.7	8127
0.7-0.8	5679
0.8-0.85	75
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC476335
0.9551	High Similarity	NPC476277
0.9404	High Similarity	NPC28724
0.9329	High Similarity	NPC476359
0.9329	High Similarity	NPC476338
0.9231	High Similarity	NPC476337
0.9133	High Similarity	NPC476362
0.9114	High Similarity	NPC476244
0.891	High Similarity	NPC476364
0.8854	High Similarity	NPC476363
0.8726	High Similarity	NPC327225
0.8599	High Similarity	NPC62354
0.8553	High Similarity	NPC25127
0.8553	High Similarity	NPC476334
0.8544	High Similarity	NPC151425
0.8487	Intermediate Similarity	NPC322021
0.8471	Intermediate Similarity	NPC474903
0.8457	Intermediate Similarity	NPC477410
0.8442	Intermediate Similarity	NPC474966
0.8438	Intermediate Similarity	NPC287504
0.8397	Intermediate Similarity	NPC30890
0.8365	Intermediate Similarity	NPC178048
0.8354	Intermediate Similarity	NPC472567
0.8344	Intermediate Similarity	NPC30720
0.8344	Intermediate Similarity	NPC472565
0.8313	Intermediate Similarity	NPC246566
0.8313	Intermediate Similarity	NPC95498
0.8278	Intermediate Similarity	NPC145769
0.8253	Intermediate Similarity	NPC476822
0.825	Intermediate Similarity	NPC163002
0.8232	Intermediate Similarity	NPC475095
0.8228	Intermediate Similarity	NPC476336
0.8217	Intermediate Similarity	NPC476843
0.8217	Intermediate Similarity	NPC476841
0.8214	Intermediate Similarity	NPC283041
0.8194	Intermediate Similarity	NPC51681
0.8187	Intermediate Similarity	NPC107739
0.8182	Intermediate Similarity	NPC472962
0.8182	Intermediate Similarity	NPC472961
0.8176	Intermediate Similarity	NPC121333
0.8176	Intermediate Similarity	NPC294972
0.8166	Intermediate Similarity	NPC152477
0.8165	Intermediate Similarity	NPC474799
0.8165	Intermediate Similarity	NPC212697
0.8155	Intermediate Similarity	NPC173292
0.8155	Intermediate Similarity	NPC20237
0.8153	Intermediate Similarity	NPC239608
0.8153	Intermediate Similarity	NPC46161
0.8148	Intermediate Similarity	NPC470340
0.8148	Intermediate Similarity	NPC180944
0.8144	Intermediate Similarity	NPC124038
0.8144	Intermediate Similarity	NPC472582
0.8141	Intermediate Similarity	NPC46180
0.814	Intermediate Similarity	NPC23593
0.8137	Intermediate Similarity	NPC472279
0.8136	Intermediate Similarity	NPC71385
0.8136	Intermediate Similarity	NPC230670
0.8129	Intermediate Similarity	NPC474784
0.8129	Intermediate Similarity	NPC4796
0.8121	Intermediate Similarity	NPC209473
0.8121	Intermediate Similarity	NPC55738
0.811	Intermediate Similarity	NPC469474
0.811	Intermediate Similarity	NPC303255
0.8107	Intermediate Similarity	NPC150131
0.8101	Intermediate Similarity	NPC474982
0.8095	Intermediate Similarity	NPC62261
0.8095	Intermediate Similarity	NPC234052
0.8095	Intermediate Similarity	NPC191930
0.8092	Intermediate Similarity	NPC327410
0.809	Intermediate Similarity	NPC112708
0.8089	Intermediate Similarity	NPC28326
0.8086	Intermediate Similarity	NPC163883
0.8086	Intermediate Similarity	NPC93498
0.8084	Intermediate Similarity	NPC48860
0.8084	Intermediate Similarity	NPC206815
0.8077	Intermediate Similarity	NPC136649
0.8077	Intermediate Similarity	NPC470991
0.8075	Intermediate Similarity	NPC177830
0.8075	Intermediate Similarity	NPC12854
0.8075	Intermediate Similarity	NPC475170
0.8072	Intermediate Similarity	NPC161947
0.8072	Intermediate Similarity	NPC310399
0.8072	Intermediate Similarity	NPC474936
0.8072	Intermediate Similarity	NPC287328
0.8072	Intermediate Similarity	NPC470183
0.8072	Intermediate Similarity	NPC155302
0.8072	Intermediate Similarity	NPC73422
0.8072	Intermediate Similarity	NPC282009
0.807	Intermediate Similarity	NPC470685
0.8065	Intermediate Similarity	NPC325625
0.8063	Intermediate Similarity	NPC98009
0.8063	Intermediate Similarity	NPC77598
0.8061	Intermediate Similarity	NPC67876
0.8061	Intermediate Similarity	NPC78071
0.8061	Intermediate Similarity	NPC471479
0.8061	Intermediate Similarity	NPC52530
0.8061	Intermediate Similarity	NPC299520
0.8061	Intermediate Similarity	NPC471515
0.8061	Intermediate Similarity	NPC129684
0.8059	Intermediate Similarity	NPC242395
0.805	Intermediate Similarity	NPC213482
0.805	Intermediate Similarity	NPC474446
0.805	Intermediate Similarity	NPC98356
0.8049	Intermediate Similarity	NPC31018
0.8049	Intermediate Similarity	NPC234485
0.8049	Intermediate Similarity	NPC255807
0.8047	Intermediate Similarity	NPC128293
0.8047	Intermediate Similarity	NPC119589
0.8047	Intermediate Similarity	NPC477517
0.8047	Intermediate Similarity	NPC235610
0.8046	Intermediate Similarity	NPC236089
0.8045	Intermediate Similarity	NPC473711
0.8038	Intermediate Similarity	NPC15743
0.8038	Intermediate Similarity	NPC16353
0.8037	Intermediate Similarity	NPC470338
0.8037	Intermediate Similarity	NPC470337
0.8037	Intermediate Similarity	NPC113608
0.8037	Intermediate Similarity	NPC146277
0.8037	Intermediate Similarity	NPC19380
0.8037	Intermediate Similarity	NPC268992
0.8037	Intermediate Similarity	NPC51824
0.8037	Intermediate Similarity	NPC323626
0.8037	Intermediate Similarity	NPC324233
0.8037	Intermediate Similarity	NPC275878
0.8036	Intermediate Similarity	NPC187491
0.8036	Intermediate Similarity	NPC319200
0.8036	Intermediate Similarity	NPC249181
0.8036	Intermediate Similarity	NPC472625
0.8035	Intermediate Similarity	NPC263955
0.8026	Intermediate Similarity	NPC239302
0.8025	Intermediate Similarity	NPC476840
0.8025	Intermediate Similarity	NPC476842
0.8025	Intermediate Similarity	NPC225854
0.8024	Intermediate Similarity	NPC471499
0.8024	Intermediate Similarity	NPC117985
0.8024	Intermediate Similarity	NPC87431
0.8024	Intermediate Similarity	NPC173137
0.8024	Intermediate Similarity	NPC308992
0.8024	Intermediate Similarity	NPC96031
0.8024	Intermediate Similarity	NPC474239
0.8024	Intermediate Similarity	NPC316457
0.8024	Intermediate Similarity	NPC201560
0.8013	Intermediate Similarity	NPC203351
0.8013	Intermediate Similarity	NPC280399
0.8013	Intermediate Similarity	NPC233961
0.8013	Intermediate Similarity	NPC339621
0.8012	Intermediate Similarity	NPC51404
0.8012	Intermediate Similarity	NPC74559
0.8012	Intermediate Similarity	NPC152904
0.8012	Intermediate Similarity	NPC279209
0.8012	Intermediate Similarity	NPC103307
0.8012	Intermediate Similarity	NPC179914
0.8012	Intermediate Similarity	NPC187792
0.8012	Intermediate Similarity	NPC102277
0.8012	Intermediate Similarity	NPC195832
0.8012	Intermediate Similarity	NPC329743
0.8012	Intermediate Similarity	NPC22192
0.8	Intermediate Similarity	NPC470456
0.8	Intermediate Similarity	NPC470762
0.8	Intermediate Similarity	NPC265511
0.8	Intermediate Similarity	NPC471500
0.8	Intermediate Similarity	NPC317383
0.8	Intermediate Similarity	NPC283081
0.8	Intermediate Similarity	NPC474167
0.8	Intermediate Similarity	NPC316769
0.8	Intermediate Similarity	NPC143892
0.8	Intermediate Similarity	NPC474638
0.8	Intermediate Similarity	NPC299090
0.8	Intermediate Similarity	NPC158761
0.8	Intermediate Similarity	NPC8965
0.8	Intermediate Similarity	NPC320825
0.8	Intermediate Similarity	NPC13858
0.8	Intermediate Similarity	NPC221383
0.8	Intermediate Similarity	NPC326037
0.7989	Intermediate Similarity	NPC29587
0.7988	Intermediate Similarity	NPC127172
0.7988	Intermediate Similarity	NPC108433
0.7988	Intermediate Similarity	NPC303950
0.7988	Intermediate Similarity	NPC472049
0.7988	Intermediate Similarity	NPC155686
0.7988	Intermediate Similarity	NPC124714
0.7988	Intermediate Similarity	NPC470457
0.7988	Intermediate Similarity	NPC300053
0.7988	Intermediate Similarity	NPC472277
0.7988	Intermediate Similarity	NPC475738
0.7988	Intermediate Similarity	NPC224280
0.7987	Intermediate Similarity	NPC232883
0.7987	Intermediate Similarity	NPC207732
0.7977	Intermediate Similarity	NPC224165
0.7976	Intermediate Similarity	NPC472635
0.7976	Intermediate Similarity	NPC474150
0.7976	Intermediate Similarity	NPC474162
0.7976	Intermediate Similarity	NPC474034
0.7976	Intermediate Similarity	NPC272722
0.7976	Intermediate Similarity	NPC474033
0.7976	Intermediate Similarity	NPC476011
0.7976	Intermediate Similarity	NPC472964
0.7975	Intermediate Similarity	NPC476434
0.7975	Intermediate Similarity	NPC262623
0.7975	Intermediate Similarity	NPC256406

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 NPC476340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	849
0.2-0.3	1893
0.3-0.4	2705
0.4-0.5	1906
0.5-0.6	1019
0.6-0.7	375
0.7-0.8	59
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.811	Intermediate Similarity	NPD3882	Suspended
0.7857	Intermediate Similarity	NPD5494	Approved
0.7831	Intermediate Similarity	NPD3817	Phase 2
0.7818	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7685	Pre-registration
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7665	Intermediate Similarity	NPD2801	Approved
0.7665	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD37	Approved
0.7602	Intermediate Similarity	NPD1247	Approved
0.7602	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.759	Intermediate Similarity	NPD4380	Phase 2
0.7546	Intermediate Similarity	NPD6799	Approved
0.7531	Intermediate Similarity	NPD6190	Approved
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD7028	Phase 2
0.7485	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD6599	Discontinued
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7808	Phase 3
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4966	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7458	Intermediate Similarity	NPD6797	Phase 2
0.7457	Intermediate Similarity	NPD6232	Discontinued
0.7455	Intermediate Similarity	NPD1512	Approved
0.7416	Intermediate Similarity	NPD7251	Discontinued
0.7414	Intermediate Similarity	NPD3926	Phase 2
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7345	Intermediate Similarity	NPD5844	Phase 1
0.7345	Intermediate Similarity	NPD7054	Approved
0.7333	Intermediate Similarity	NPD1511	Approved
0.731	Intermediate Similarity	NPD5402	Approved
0.7303	Intermediate Similarity	NPD7472	Approved
0.7299	Intermediate Similarity	NPD8127	Discontinued
0.7296	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD5763	Approved
0.7284	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7819	Suspended
0.7251	Intermediate Similarity	NPD5761	Phase 2
0.7251	Intermediate Similarity	NPD5760	Phase 2
0.7247	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1240	Approved
0.7225	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2796	Approved
0.7213	Intermediate Similarity	NPD8434	Phase 2
0.7191	Intermediate Similarity	NPD7228	Approved
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7186	Intermediate Similarity	NPD2533	Approved
0.7186	Intermediate Similarity	NPD2534	Approved
0.7186	Intermediate Similarity	NPD2532	Approved
0.7179	Intermediate Similarity	NPD5647	Approved
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD1607	Approved
0.7134	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1549	Phase 2
0.7134	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD943	Approved
0.7125	Intermediate Similarity	NPD3620	Phase 2
0.711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5353	Approved
0.7101	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2800	Approved
0.7083	Intermediate Similarity	NPD5401	Approved
0.7079	Intermediate Similarity	NPD2403	Approved
0.7073	Intermediate Similarity	NPD6002	Phase 3
0.7073	Intermediate Similarity	NPD6005	Phase 3
0.7073	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6004	Phase 3
0.7073	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7033	Intermediate Similarity	NPD6559	Discontinued
0.7033	Intermediate Similarity	NPD7240	Approved
0.7033	Intermediate Similarity	NPD6764	Approved
0.7033	Intermediate Similarity	NPD6765	Approved
0.703	Intermediate Similarity	NPD2424	Discontinued
0.7024	Intermediate Similarity	NPD4357	Discontinued
0.7022	Intermediate Similarity	NPD5242	Approved
0.7019	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5536	Phase 2
0.6964	Remote Similarity	NPD7236	Approved
0.6954	Remote Similarity	NPD1465	Phase 2
0.6946	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6273	Approved
0.6936	Remote Similarity	NPD7411	Suspended
0.6933	Remote Similarity	NPD6651	Approved
0.691	Remote Similarity	NPD6959	Discontinued
0.6909	Remote Similarity	NPD2935	Discontinued
0.6909	Remote Similarity	NPD6100	Approved
0.6909	Remote Similarity	NPD6099	Approved
0.6906	Remote Similarity	NPD7799	Discontinued
0.6901	Remote Similarity	NPD920	Approved
0.6882	Remote Similarity	NPD6785	Approved
0.6882	Remote Similarity	NPD6784	Approved
0.6871	Remote Similarity	NPD5735	Approved
0.6871	Remote Similarity	NPD447	Suspended
0.6862	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1653	Approved
0.6852	Remote Similarity	NPD6233	Phase 2
0.6848	Remote Similarity	NPD7033	Discontinued
0.6845	Remote Similarity	NPD8150	Discontinued
0.6839	Remote Similarity	NPD5090	Approved
0.6839	Remote Similarity	NPD5089	Approved
0.6835	Remote Similarity	NPD1876	Approved
0.6821	Remote Similarity	NPD5283	Phase 1
0.6818	Remote Similarity	NPD5977	Approved
0.6818	Remote Similarity	NPD5978	Approved
0.681	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3094	Phase 2
0.679	Remote Similarity	NPD6798	Discontinued
0.6784	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7229	Phase 3
0.6772	Remote Similarity	NPD2982	Phase 2
0.6772	Remote Similarity	NPD2983	Phase 2
0.677	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7239	Suspended
0.675	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2799	Discontinued
0.6746	Remote Similarity	NPD3750	Approved
0.6746	Remote Similarity	NPD8166	Discontinued
0.6743	Remote Similarity	NPD6386	Approved
0.6743	Remote Similarity	NPD6385	Approved
0.6742	Remote Similarity	NPD3749	Approved
0.6736	Remote Similarity	NPD2973	Approved
0.6736	Remote Similarity	NPD2974	Approved
0.6736	Remote Similarity	NPD2975	Approved
0.6728	Remote Similarity	NPD7095	Approved
0.6726	Remote Similarity	NPD5958	Discontinued
0.6721	Remote Similarity	NPD2163	Approved
0.6718	Remote Similarity	NPD6782	Approved
0.6718	Remote Similarity	NPD4580	Approved
0.6718	Remote Similarity	NPD6776	Approved
0.6718	Remote Similarity	NPD6780	Approved
0.6718	Remote Similarity	NPD6781	Approved
0.6718	Remote Similarity	NPD6779	Approved
0.6718	Remote Similarity	NPD6777	Approved
0.6718	Remote Similarity	NPD6778	Approved
0.6709	Remote Similarity	NPD9269	Phase 2
0.6709	Remote Similarity	NPD1608	Approved
0.6709	Remote Similarity	NPD2981	Phase 2
0.6708	Remote Similarity	NPD3018	Phase 2
0.6708	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5712	Approved
0.6707	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD4060	Phase 1
0.6703	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7435	Discontinued
0.6701	Remote Similarity	NPD7497	Discontinued
0.6687	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6362	Approved
0.6686	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3146	Approved
0.6686	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1243	Approved
0.6685	Remote Similarity	NPD5711	Approved
0.6685	Remote Similarity	NPD5710	Approved
0.6685	Remote Similarity	NPD7768	Phase 2
0.6684	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2494	Approved
0.6684	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4582	Approved
0.6667	Remote Similarity	NPD9268	Approved
0.6667	Remote Similarity	NPD4583	Approved
0.6667	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3657	Discovery
0.6667	Remote Similarity	NPD5124	Phase 1
0.665	Remote Similarity	NPD4665	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