NPASS Compound

Structure

NPC476334 OpenBabel07101719132D 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 1 0 0 0 0 0 0 0 0 0 0.6481 -0.7198 0.0000 C 0 0 1 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 1 0 0 0 20 24 1 0 0 0 0 21 22 1 1 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:	420.21
Volume:	429.044
LogP:	2.44
LogD:	2.599
LogS:	-2.071
# Rotatable Bonds:	8
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	5.399
Fsp3:	0.565
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:	-4.775
MDCK Permeability:	4.4186530431034043e-05
Pgp-inhibitor:	0.257
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.567

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.614
Plasma Protein Binding (PPB):	57.29072570800781%
Volume Distribution (VD):	1.102
Pgp-substrate:	24.29935073852539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.644
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	8.155
Half-life (T1/2):	0.695

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.634
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.136
Carcinogencity:	0.106
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC476334

Natural Product ID:	NPC476334
*Common Name:**	Nectamazin C
IUPAC Name:	(1S,4S,5S,6R,7S,8S)-1,5-dimethoxy-7-methyl-3-prop-2-enyl-6-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-2-ene-4,8-diol
Synonyms:	Nectamazin C
Standard InCHIKey:	OHVTXDBRSOSKKO-BHIPVSGSSA-N
Standard InCHI:	InChI=1S/C23H32O7/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/h8,10-13,18,20-21,24-25H,1,9H2,2-7H3/t13-,18+,20-,21-,22+,23-/m0/s1
SMILES:	C=CCC1=C[C@@]2(OC)[C@H]([C@@H]([C@]([C@H]1O)([C@H]2O)OC)c1cc(OC)c(c(c1)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL570290
PubChem CID:	45487137
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]
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]
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	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	=	74600.0	nM	PMID[515733]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	6830.0	nM	PMID[515733]
NPT2	Others	Unspecified		IC50	=	12800.0	nM	PMID[515733]
NPT2	Others	Unspecified		Ratio IC50	=	10.9	n.a.	PMID[515733]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3780.0	nM	PMID[515733]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21600.0	nM	PMID[515733]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	999000.0	nM	PMID[515733]

☑ 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 NPC476334 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	420
0.1-0.2	1331
0.2-0.3	3666
0.3-0.4	9875
0.4-0.5	9343
0.5-0.6	6024
0.6-0.7	9082
0.7-0.8	2451
0.8-0.85	448
0.85-0.9	56
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8759	High Similarity	NPC474017
0.8716	High Similarity	NPC28724
0.8705	High Similarity	NPC287745
0.869	High Similarity	NPC211758
0.869	High Similarity	NPC87794
0.8652	High Similarity	NPC477938
0.8643	High Similarity	NPC256262
0.8633	High Similarity	NPC158331
0.8613	High Similarity	NPC170844
0.8613	High Similarity	NPC476968
0.8611	High Similarity	NPC184607
0.8609	High Similarity	NPC189730
0.8603	High Similarity	NPC242032
0.8601	High Similarity	NPC87725
0.8601	High Similarity	NPC263261
0.8591	High Similarity	NPC476335
0.8571	High Similarity	NPC244983
0.8571	High Similarity	NPC326095
0.8561	High Similarity	NPC18842
0.8561	High Similarity	NPC175067
0.8561	High Similarity	NPC204215
0.8553	High Similarity	NPC476340
0.8552	High Similarity	NPC317237
0.8552	High Similarity	NPC277951
0.8552	High Similarity	NPC44530
0.8543	High Similarity	NPC164152
0.8542	High Similarity	NPC470937
0.854	High Similarity	NPC470213
0.854	High Similarity	NPC98631
0.854	High Similarity	NPC470084
0.854	High Similarity	NPC206615
0.854	High Similarity	NPC186843
0.8511	High Similarity	NPC99572
0.8511	High Similarity	NPC126409
0.8493	Intermediate Similarity	NPC181615
0.8489	Intermediate Similarity	NPC470096
0.8489	Intermediate Similarity	NPC30043
0.8489	Intermediate Similarity	NPC470095
0.8489	Intermediate Similarity	NPC469625
0.8489	Intermediate Similarity	NPC469613
0.8489	Intermediate Similarity	NPC277804
0.8483	Intermediate Similarity	NPC155392
0.8483	Intermediate Similarity	NPC135767
0.8483	Intermediate Similarity	NPC274721
0.8478	Intermediate Similarity	NPC158477
0.8478	Intermediate Similarity	NPC222004
0.8478	Intermediate Similarity	NPC285339
0.8478	Intermediate Similarity	NPC469963
0.8478	Intermediate Similarity	NPC470258
0.8478	Intermediate Similarity	NPC469951
0.8478	Intermediate Similarity	NPC190629
0.8478	Intermediate Similarity	NPC210623
0.8478	Intermediate Similarity	NPC3439
0.8478	Intermediate Similarity	NPC212015
0.8478	Intermediate Similarity	NPC226788
0.8478	Intermediate Similarity	NPC273295
0.8478	Intermediate Similarity	NPC218856
0.8478	Intermediate Similarity	NPC202582
0.8467	Intermediate Similarity	NPC118533
0.8467	Intermediate Similarity	NPC127587
0.8467	Intermediate Similarity	NPC165045
0.8467	Intermediate Similarity	NPC5428
0.8462	Intermediate Similarity	NPC184613
0.8452	Intermediate Similarity	NPC476244
0.8444	Intermediate Similarity	NPC165375
0.8444	Intermediate Similarity	NPC220598
0.844	Intermediate Similarity	NPC16485
0.8435	Intermediate Similarity	NPC260397
0.8429	Intermediate Similarity	NPC201587
0.8429	Intermediate Similarity	NPC470752
0.8429	Intermediate Similarity	NPC253105
0.8429	Intermediate Similarity	NPC6451
0.8417	Intermediate Similarity	NPC469614
0.8417	Intermediate Similarity	NPC153739
0.8417	Intermediate Similarity	NPC469612
0.8417	Intermediate Similarity	NPC192687
0.8417	Intermediate Similarity	NPC257582
0.8417	Intermediate Similarity	NPC241522
0.8417	Intermediate Similarity	NPC242807
0.8417	Intermediate Similarity	NPC64201
0.8417	Intermediate Similarity	NPC92164
0.8417	Intermediate Similarity	NPC145305
0.8417	Intermediate Similarity	NPC77040
0.8417	Intermediate Similarity	NPC224157
0.8417	Intermediate Similarity	NPC174495
0.8417	Intermediate Similarity	NPC42300
0.8417	Intermediate Similarity	NPC187998
0.8403	Intermediate Similarity	NPC309124
0.8403	Intermediate Similarity	NPC254759
0.8403	Intermediate Similarity	NPC184797
0.8403	Intermediate Similarity	NPC160283
0.8403	Intermediate Similarity	NPC291101
0.8403	Intermediate Similarity	NPC266197
0.8394	Intermediate Similarity	NPC50683
0.8394	Intermediate Similarity	NPC186845
0.8394	Intermediate Similarity	NPC206882
0.8394	Intermediate Similarity	NPC9891
0.8394	Intermediate Similarity	NPC76451
0.8394	Intermediate Similarity	NPC112571
0.8394	Intermediate Similarity	NPC285725
0.8394	Intermediate Similarity	NPC88297
0.8392	Intermediate Similarity	NPC474039
0.8392	Intermediate Similarity	NPC86605
0.8392	Intermediate Similarity	NPC301765
0.8392	Intermediate Similarity	NPC156948
0.8392	Intermediate Similarity	NPC46277
0.8392	Intermediate Similarity	NPC3072
0.838	Intermediate Similarity	NPC61946
0.838	Intermediate Similarity	NPC174191
0.838	Intermediate Similarity	NPC165155
0.838	Intermediate Similarity	NPC24490
0.838	Intermediate Similarity	NPC34103
0.838	Intermediate Similarity	NPC141765
0.8369	Intermediate Similarity	NPC26394
0.8369	Intermediate Similarity	NPC263064
0.8369	Intermediate Similarity	NPC475840
0.8369	Intermediate Similarity	NPC196937
0.8357	Intermediate Similarity	NPC232275
0.8357	Intermediate Similarity	NPC309787
0.8357	Intermediate Similarity	NPC474356
0.8357	Intermediate Similarity	NPC12275
0.8357	Intermediate Similarity	NPC472597
0.8357	Intermediate Similarity	NPC45715
0.8356	Intermediate Similarity	NPC477616
0.8346	Intermediate Similarity	NPC135961
0.8345	Intermediate Similarity	NPC475875
0.8345	Intermediate Similarity	NPC190144
0.8345	Intermediate Similarity	NPC471389
0.8345	Intermediate Similarity	NPC311530
0.8333	Intermediate Similarity	NPC474119
0.8333	Intermediate Similarity	NPC74817
0.8333	Intermediate Similarity	NPC471388
0.8333	Intermediate Similarity	NPC246620
0.8333	Intermediate Similarity	NPC6300
0.8333	Intermediate Similarity	NPC70682
0.8333	Intermediate Similarity	NPC82679
0.8333	Intermediate Similarity	NPC471183
0.8333	Intermediate Similarity	NPC124452
0.8333	Intermediate Similarity	NPC169474
0.8333	Intermediate Similarity	NPC473739
0.8333	Intermediate Similarity	NPC236306
0.8333	Intermediate Similarity	NPC260741
0.8333	Intermediate Similarity	NPC232164
0.8333	Intermediate Similarity	NPC159968
0.8333	Intermediate Similarity	NPC114171
0.8333	Intermediate Similarity	NPC230124
0.8333	Intermediate Similarity	NPC236791
0.8333	Intermediate Similarity	NPC324112
0.8333	Intermediate Similarity	NPC282000
0.8333	Intermediate Similarity	NPC292882
0.8333	Intermediate Similarity	NPC293054
0.8322	Intermediate Similarity	NPC10737
0.8322	Intermediate Similarity	NPC477939
0.8322	Intermediate Similarity	NPC16435
0.8322	Intermediate Similarity	NPC162659
0.8322	Intermediate Similarity	NPC227503
0.8322	Intermediate Similarity	NPC472334
0.8322	Intermediate Similarity	NPC472336
0.8322	Intermediate Similarity	NPC29799
0.8322	Intermediate Similarity	NPC54743
0.8322	Intermediate Similarity	NPC133025
0.8322	Intermediate Similarity	NPC177160
0.8322	Intermediate Similarity	NPC248727
0.8322	Intermediate Similarity	NPC230734
0.8322	Intermediate Similarity	NPC306441
0.8322	Intermediate Similarity	NPC126101
0.8322	Intermediate Similarity	NPC265433
0.8322	Intermediate Similarity	NPC327735
0.8322	Intermediate Similarity	NPC302701
0.8322	Intermediate Similarity	NPC156502
0.8322	Intermediate Similarity	NPC269091
0.8322	Intermediate Similarity	NPC474639
0.8322	Intermediate Similarity	NPC270456
0.8322	Intermediate Similarity	NPC209985
0.8322	Intermediate Similarity	NPC263367
0.8321	Intermediate Similarity	NPC251855
0.8321	Intermediate Similarity	NPC117214
0.8321	Intermediate Similarity	NPC233410
0.8321	Intermediate Similarity	NPC148627
0.8321	Intermediate Similarity	NPC472093
0.8321	Intermediate Similarity	NPC193544
0.8321	Intermediate Similarity	NPC208950
0.8321	Intermediate Similarity	NPC17943
0.8321	Intermediate Similarity	NPC203133
0.8321	Intermediate Similarity	NPC221077
0.8321	Intermediate Similarity	NPC475169
0.8321	Intermediate Similarity	NPC57490
0.8321	Intermediate Similarity	NPC116907
0.8321	Intermediate Similarity	NPC298757
0.8321	Intermediate Similarity	NPC105925
0.8311	Intermediate Similarity	NPC474234
0.8311	Intermediate Similarity	NPC317053
0.8311	Intermediate Similarity	NPC324492
0.831	Intermediate Similarity	NPC209199
0.831	Intermediate Similarity	NPC311256
0.8309	Intermediate Similarity	NPC282496
0.8309	Intermediate Similarity	NPC233526
0.8299	Intermediate Similarity	NPC93323
0.8299	Intermediate Similarity	NPC471415
0.8299	Intermediate Similarity	NPC45257

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 NPC476334 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	833
0.2-0.3	1981
0.3-0.4	2787
0.4-0.5	1741
0.5-0.6	1004
0.6-0.7	409
0.7-0.8	63
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
0.8613	High Similarity	NPD3027	Phase 3
0.8042	Intermediate Similarity	NPD1613	Approved
0.8042	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3620	Phase 2
0.7872	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5735	Approved
0.7718	Intermediate Similarity	NPD5763	Approved
0.7718	Intermediate Similarity	NPD5762	Approved
0.7707	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3094	Phase 2
0.763	Intermediate Similarity	NPD5283	Phase 1
0.7569	Intermediate Similarity	NPD2861	Phase 2
0.7569	Intermediate Similarity	NPD3018	Phase 2
0.7568	Intermediate Similarity	NPD6653	Approved
0.7562	Intermediate Similarity	NPD4967	Phase 2
0.7562	Intermediate Similarity	NPD4965	Approved
0.7562	Intermediate Similarity	NPD4966	Approved
0.7535	Intermediate Similarity	NPD2982	Phase 2
0.7535	Intermediate Similarity	NPD4749	Approved
0.7535	Intermediate Similarity	NPD2983	Phase 2
0.7534	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7481	Intermediate Similarity	NPD228	Approved
0.7469	Intermediate Similarity	NPD6234	Discontinued
0.7465	Intermediate Similarity	NPD2981	Phase 2
0.7407	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1610	Phase 2
0.7394	Intermediate Similarity	NPD3705	Approved
0.7394	Intermediate Similarity	NPD3092	Approved
0.7386	Intermediate Similarity	NPD6674	Discontinued
0.7383	Intermediate Similarity	NPD3657	Discovery
0.7379	Intermediate Similarity	NPD4624	Approved
0.7365	Intermediate Similarity	NPD7228	Approved
0.7361	Intermediate Similarity	NPD8651	Approved
0.7333	Intermediate Similarity	NPD6353	Approved
0.7315	Intermediate Similarity	NPD2238	Phase 2
0.7305	Intermediate Similarity	NPD1357	Approved
0.7294	Intermediate Similarity	NPD7685	Pre-registration
0.7292	Intermediate Similarity	NPD5327	Phase 3
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1934	Approved
0.7266	Intermediate Similarity	NPD7157	Approved
0.7255	Intermediate Similarity	NPD6005	Phase 3
0.7255	Intermediate Similarity	NPD6004	Phase 3
0.7255	Intermediate Similarity	NPD6002	Phase 3
0.7255	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1653	Approved
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7226	Intermediate Similarity	NPD3892	Phase 2
0.7222	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4140	Approved
0.7179	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7843	Approved
0.7171	Intermediate Similarity	NPD6111	Discontinued
0.7169	Intermediate Similarity	NPD8127	Discontinued
0.7161	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7134	Intermediate Similarity	NPD7124	Phase 2
0.7132	Intermediate Similarity	NPD2684	Approved
0.7113	Intermediate Similarity	NPD3091	Approved
0.7113	Intermediate Similarity	NPD1548	Phase 1
0.7113	Intermediate Similarity	NPD7741	Discontinued
0.7093	Intermediate Similarity	NPD7240	Approved
0.7086	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD4005	Discontinued
0.708	Intermediate Similarity	NPD4750	Phase 3
0.708	Intermediate Similarity	NPD3021	Approved
0.708	Intermediate Similarity	NPD3022	Approved
0.7073	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4236	Phase 3
0.7051	Intermediate Similarity	NPD4237	Approved
0.7051	Intermediate Similarity	NPD5177	Phase 3
0.7041	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6166	Phase 2
0.7039	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD3540	Phase 1
0.7032	Intermediate Similarity	NPD1375	Discontinued
0.703	Intermediate Similarity	NPD3882	Suspended
0.7029	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6671	Approved
0.7018	Intermediate Similarity	NPD5844	Phase 1
0.7014	Intermediate Similarity	NPD3095	Discontinued
0.7012	Intermediate Similarity	NPD2801	Approved
0.7006	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.7006	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD5494	Approved
0.7006	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7473	Discontinued
0.6987	Remote Similarity	NPD2424	Discontinued
0.6981	Remote Similarity	NPD4357	Discontinued
0.6977	Remote Similarity	NPD7074	Phase 3
0.6975	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2560	Approved
0.697	Remote Similarity	NPD2563	Approved
0.6968	Remote Similarity	NPD3539	Phase 1
0.6968	Remote Similarity	NPD2161	Phase 2
0.6962	Remote Similarity	NPD2219	Phase 1
0.6959	Remote Similarity	NPD3818	Discontinued
0.6959	Remote Similarity	NPD6362	Approved
0.6954	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4538	Approved
0.6948	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4536	Approved
0.6943	Remote Similarity	NPD3060	Approved
0.6943	Remote Similarity	NPD1652	Phase 2
0.6934	Remote Similarity	NPD290	Approved
0.6933	Remote Similarity	NPD4675	Approved
0.6933	Remote Similarity	NPD4678	Approved
0.6933	Remote Similarity	NPD4380	Phase 2
0.6928	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD7266	Discontinued
0.6919	Remote Similarity	NPD7054	Approved
0.6918	Remote Similarity	NPD5058	Phase 3
0.6903	Remote Similarity	NPD5588	Approved
0.6894	Remote Similarity	NPD52	Approved
0.6894	Remote Similarity	NPD7526	Approved
0.6894	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6696	Suspended
0.6882	Remote Similarity	NPD2969	Approved
0.6882	Remote Similarity	NPD2970	Approved
0.6879	Remote Similarity	NPD7472	Approved
0.6871	Remote Similarity	NPD2233	Approved
0.6871	Remote Similarity	NPD2232	Approved
0.6871	Remote Similarity	NPD2230	Approved
0.6867	Remote Similarity	NPD3817	Phase 2
0.6859	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD6099	Approved
0.6855	Remote Similarity	NPD2677	Approved
0.6824	Remote Similarity	NPD6071	Discontinued
0.6818	Remote Similarity	NPD7313	Approved
0.6818	Remote Similarity	NPD7312	Approved
0.6818	Remote Similarity	NPD7311	Approved
0.6818	Remote Similarity	NPD7310	Approved
0.6815	Remote Similarity	NPD940	Approved
0.6815	Remote Similarity	NPD846	Approved
0.6807	Remote Similarity	NPD5773	Approved
0.6807	Remote Similarity	NPD5772	Approved
0.6806	Remote Similarity	NPD5536	Phase 2
0.6803	Remote Similarity	NPD422	Phase 1
0.68	Remote Similarity	NPD5647	Approved
0.6797	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5960	Phase 3
0.679	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4626	Approved
0.6781	Remote Similarity	NPD4059	Approved
0.678	Remote Similarity	NPD7309	Approved
0.6776	Remote Similarity	NPD7095	Approved
0.6774	Remote Similarity	NPD2157	Approved
0.6774	Remote Similarity	NPD4097	Suspended
0.677	Remote Similarity	NPD1511	Approved
0.677	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7808	Phase 3
0.6761	Remote Similarity	NPD7549	Discontinued
0.6755	Remote Similarity	NPD5736	Approved
0.6753	Remote Similarity	NPD1558	Phase 1
0.6748	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD27	Approved
0.6744	Remote Similarity	NPD2489	Approved
0.6732	Remote Similarity	NPD5111	Phase 2
0.6732	Remote Similarity	NPD5109	Approved
0.6732	Remote Similarity	NPD5110	Phase 2
0.6731	Remote Similarity	NPD7097	Phase 1
0.6728	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3051	Approved
0.671	Remote Similarity	NPD230	Phase 1
0.6709	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5761	Phase 2
0.6707	Remote Similarity	NPD3686	Approved
0.6707	Remote Similarity	NPD3687	Approved
0.6707	Remote Similarity	NPD4210	Discontinued
0.6707	Remote Similarity	NPD2977	Approved
0.6707	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2978	Approved
0.6707	Remote Similarity	NPD5760	Phase 2
0.6705	Remote Similarity	NPD7251	Discontinued
0.6704	Remote Similarity	NPD4663	Approved
0.6691	Remote Similarity	NPD291	Approved
0.6688	Remote Similarity	NPD2674	Phase 3
0.6688	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1512	Approved
0.6687	Remote Similarity	NPD5089	Approved
0.6687	Remote Similarity	NPD7466	Approved
0.6687	Remote Similarity	NPD5090	Approved
0.6687	Remote Similarity	NPD7615	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