NPASS Compound

Structure

NPC474539 OpenBabel07101719132D 27 28 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6797 3.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7479 2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0656 0.0086 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8692 0.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1280 1.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -6.4209 2.2247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4550 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.0000 0.0000 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 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 3 17 2 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 16 2 1 1 0 0 0 16 17 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 25 2 0 0 0 0 22 27 1 0 0 0 0 23 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.23
Volume:	408.593
LogP:	5.253
LogD:	3.992
LogS:	-5.268
# Rotatable Bonds:	6
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.08
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	2.4305150873260573e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	99.87826538085938%
Volume Distribution (VD):	3.794
Pgp-substrate:	1.6151180267333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.806
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.255
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.804
CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.618

ADMET: Excretion

Clearance (CL):	2.498
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.649
Maximum Recommended Daily Dose:	0.605
Skin Sensitization:	0.956
Carcinogencity:	0.152
Eye Corrosion:	0.004
Eye Irritation:	0.719
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC474539

Natural Product ID:	NPC474539
*Common Name:**	Metachromin A Monomethylate
IUPAC Name:	3-[(E)-5-[(1R,3R)-1,3-dimethyl-2-methylidenecyclohexyl]-3-methylpent-2-enyl]-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	Metachromin A Monomethylate
Standard InCHIKey:	AZBHZNBFRZPJFT-FFWZJQPYSA-N
Standard InCHI:	InChI=1S/C23H32O4/c1-15(11-13-23(4)12-7-8-16(2)17(23)3)9-10-18-21(25)20(26-5)14-19(24)22(18)27-6/h9,14,16H,3,7-8,10-13H2,1-2,4-6H3/b15-9+/t16-,23-/m1/s1
SMILES:	COC1=C(C/C=C(/CC[C@@]2(C)CCC[C@H](C2=C)C)C)C(=O)C(=CC1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471292
PubChem CID:	11164649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO33163	hippospongia metachromia	Species	Spongiidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11421749]
NPO33163	hippospongia metachromia	Species	Spongiidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[2607352]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[465822]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[465822]

☑ 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 NPC474539 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	170
0.1-0.2	1405
0.2-0.3	7465
0.3-0.4	17962
0.4-0.5	8952
0.5-0.6	5350
0.6-0.7	1290
0.7-0.8	89
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC147438
0.8889	High Similarity	NPC26504
0.8312	Intermediate Similarity	NPC474085
0.8267	Intermediate Similarity	NPC283087
0.8125	Intermediate Similarity	NPC8518
0.8125	Intermediate Similarity	NPC6185
0.8125	Intermediate Similarity	NPC263997
0.8125	Intermediate Similarity	NPC241512
0.8125	Intermediate Similarity	NPC132228
0.8101	Intermediate Similarity	NPC288281
0.8077	Intermediate Similarity	NPC99308
0.7901	Intermediate Similarity	NPC133652
0.7895	Intermediate Similarity	NPC110725
0.7848	Intermediate Similarity	NPC475833
0.7778	Intermediate Similarity	NPC474619
0.7761	Intermediate Similarity	NPC299369
0.7761	Intermediate Similarity	NPC224103
0.7761	Intermediate Similarity	NPC200831
0.7746	Intermediate Similarity	NPC98897
0.7692	Intermediate Similarity	NPC23778
0.7647	Intermediate Similarity	NPC223093
0.7639	Intermediate Similarity	NPC16119
0.7625	Intermediate Similarity	NPC55869
0.7606	Intermediate Similarity	NPC34622
0.7606	Intermediate Similarity	NPC474400
0.7595	Intermediate Similarity	NPC27817
0.7576	Intermediate Similarity	NPC317796
0.7531	Intermediate Similarity	NPC103486
0.75	Intermediate Similarity	NPC108955
0.747	Intermediate Similarity	NPC474680
0.747	Intermediate Similarity	NPC32037
0.7468	Intermediate Similarity	NPC478246
0.7468	Intermediate Similarity	NPC478247
0.7467	Intermediate Similarity	NPC291062
0.7467	Intermediate Similarity	NPC94743
0.7465	Intermediate Similarity	NPC151728
0.7465	Intermediate Similarity	NPC57463
0.7442	Intermediate Similarity	NPC474209
0.7442	Intermediate Similarity	NPC475823
0.7439	Intermediate Similarity	NPC8091
0.7436	Intermediate Similarity	NPC1254
0.7432	Intermediate Similarity	NPC263382
0.7432	Intermediate Similarity	NPC146376
0.7432	Intermediate Similarity	NPC125578
0.7432	Intermediate Similarity	NPC155198
0.7424	Intermediate Similarity	NPC474805
0.7412	Intermediate Similarity	NPC53454
0.7403	Intermediate Similarity	NPC264178
0.7375	Intermediate Similarity	NPC476177
0.7333	Intermediate Similarity	NPC474060
0.7333	Intermediate Similarity	NPC262673
0.7326	Intermediate Similarity	NPC280833
0.7308	Intermediate Similarity	NPC175079
0.7297	Intermediate Similarity	NPC243272
0.7286	Intermediate Similarity	NPC473494
0.7273	Intermediate Similarity	NPC144947
0.7262	Intermediate Similarity	NPC255174
0.7262	Intermediate Similarity	NPC90287
0.7262	Intermediate Similarity	NPC470177
0.726	Intermediate Similarity	NPC251118
0.725	Intermediate Similarity	NPC469996
0.7229	Intermediate Similarity	NPC105803
0.7215	Intermediate Similarity	NPC474463
0.7215	Intermediate Similarity	NPC40353
0.72	Intermediate Similarity	NPC188292
0.72	Intermediate Similarity	NPC260474
0.72	Intermediate Similarity	NPC134385
0.7195	Intermediate Similarity	NPC149237
0.7195	Intermediate Similarity	NPC225515
0.7183	Intermediate Similarity	NPC127582
0.7179	Intermediate Similarity	NPC238146
0.7176	Intermediate Similarity	NPC472863
0.7143	Intermediate Similarity	NPC139056
0.7143	Intermediate Similarity	NPC60772
0.7125	Intermediate Similarity	NPC472300
0.7123	Intermediate Similarity	NPC52449
0.7123	Intermediate Similarity	NPC169275
0.7121	Intermediate Similarity	NPC22329
0.7108	Intermediate Similarity	NPC321289
0.7108	Intermediate Similarity	NPC327969
0.7105	Intermediate Similarity	NPC256846
0.7105	Intermediate Similarity	NPC94488
0.7093	Intermediate Similarity	NPC38885
0.7089	Intermediate Similarity	NPC65650
0.7079	Intermediate Similarity	NPC263780
0.7073	Intermediate Similarity	NPC2482
0.7073	Intermediate Similarity	NPC74086
0.7051	Intermediate Similarity	NPC474228
0.7051	Intermediate Similarity	NPC303613
0.7045	Intermediate Similarity	NPC38952
0.7037	Intermediate Similarity	NPC30321
0.7037	Intermediate Similarity	NPC189485
0.7024	Intermediate Similarity	NPC53733
0.7013	Intermediate Similarity	NPC251929
0.7013	Intermediate Similarity	NPC2634
0.7013	Intermediate Similarity	NPC265782
0.7	Intermediate Similarity	NPC470525
0.7	Intermediate Similarity	NPC180886
0.7	Intermediate Similarity	NPC92080
0.7	Intermediate Similarity	NPC112680
0.7	Intermediate Similarity	NPC292589
0.7	Intermediate Similarity	NPC23170
0.6988	Remote Similarity	NPC470034
0.6988	Remote Similarity	NPC478262
0.6988	Remote Similarity	NPC472684
0.6988	Remote Similarity	NPC189237
0.6988	Remote Similarity	NPC475863
0.6988	Remote Similarity	NPC44963
0.6988	Remote Similarity	NPC278459
0.6988	Remote Similarity	NPC116797
0.6986	Remote Similarity	NPC288253
0.6977	Remote Similarity	NPC220478
0.6977	Remote Similarity	NPC203795
0.6974	Remote Similarity	NPC310992
0.6974	Remote Similarity	NPC87141
0.697	Remote Similarity	NPC220191
0.697	Remote Similarity	NPC228776
0.6966	Remote Similarity	NPC470036
0.6966	Remote Similarity	NPC174167
0.6962	Remote Similarity	NPC474796
0.6962	Remote Similarity	NPC474797
0.6962	Remote Similarity	NPC20025
0.6962	Remote Similarity	NPC329866
0.6962	Remote Similarity	NPC309852
0.6951	Remote Similarity	NPC475681
0.6947	Remote Similarity	NPC179208
0.6941	Remote Similarity	NPC53385
0.6941	Remote Similarity	NPC320801
0.6941	Remote Similarity	NPC472265
0.6941	Remote Similarity	NPC474359
0.6932	Remote Similarity	NPC210216
0.6932	Remote Similarity	NPC305039
0.6923	Remote Similarity	NPC474884
0.6923	Remote Similarity	NPC474562
0.6923	Remote Similarity	NPC190035
0.6923	Remote Similarity	NPC54123
0.6912	Remote Similarity	NPC23117
0.6901	Remote Similarity	NPC311852
0.6901	Remote Similarity	NPC56905
0.6901	Remote Similarity	NPC27610
0.6892	Remote Similarity	NPC4638
0.6892	Remote Similarity	NPC212210
0.6892	Remote Similarity	NPC7029
0.6892	Remote Similarity	NPC285371
0.6892	Remote Similarity	NPC475124
0.6883	Remote Similarity	NPC139397
0.6875	Remote Similarity	NPC474885
0.6875	Remote Similarity	NPC40170
0.6867	Remote Similarity	NPC304795
0.6867	Remote Similarity	NPC287063
0.686	Remote Similarity	NPC189311
0.686	Remote Similarity	NPC33881
0.686	Remote Similarity	NPC469993
0.6854	Remote Similarity	NPC472325
0.6854	Remote Similarity	NPC471818
0.6849	Remote Similarity	NPC228574
0.6849	Remote Similarity	NPC60565
0.6849	Remote Similarity	NPC294304
0.6842	Remote Similarity	NPC4370
0.6842	Remote Similarity	NPC290350
0.6842	Remote Similarity	NPC176107
0.6835	Remote Similarity	NPC251705
0.6835	Remote Similarity	NPC470045
0.6835	Remote Similarity	NPC470044
0.6829	Remote Similarity	NPC321514
0.6829	Remote Similarity	NPC471409
0.6829	Remote Similarity	NPC275494
0.6829	Remote Similarity	NPC475994
0.6829	Remote Similarity	NPC115515
0.6829	Remote Similarity	NPC74410
0.6829	Remote Similarity	NPC62336
0.6829	Remote Similarity	NPC99182
0.6824	Remote Similarity	NPC291999
0.6824	Remote Similarity	NPC309309
0.6818	Remote Similarity	NPC478261
0.6818	Remote Similarity	NPC478259
0.6818	Remote Similarity	NPC478260
0.6818	Remote Similarity	NPC185059
0.6818	Remote Similarity	NPC475001
0.6813	Remote Similarity	NPC476596
0.6806	Remote Similarity	NPC276764
0.6806	Remote Similarity	NPC472304
0.6795	Remote Similarity	NPC282593
0.6795	Remote Similarity	NPC35734
0.6795	Remote Similarity	NPC307176
0.6795	Remote Similarity	NPC203819
0.6795	Remote Similarity	NPC260040
0.6795	Remote Similarity	NPC286154
0.6795	Remote Similarity	NPC469660
0.6795	Remote Similarity	NPC159577
0.679	Remote Similarity	NPC27205
0.679	Remote Similarity	NPC263582
0.679	Remote Similarity	NPC250621
0.679	Remote Similarity	NPC69408
0.6786	Remote Similarity	NPC6663
0.6786	Remote Similarity	NPC474353
0.6786	Remote Similarity	NPC90055
0.6786	Remote Similarity	NPC121984
0.6782	Remote Similarity	NPC291712
0.6782	Remote Similarity	NPC94666

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 NPC474539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1694
0.2-0.3	4608
0.3-0.4	2056
0.4-0.5	343
0.5-0.6	219
0.6-0.7	63
0.7-0.8	4
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
0.7761	Intermediate Similarity	NPD8779	Phase 3
0.7722	Intermediate Similarity	NPD4695	Discontinued
0.7639	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5737	Approved
0.7209	Intermediate Similarity	NPD6672	Approved
0.7073	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4691	Approved
0.6932	Remote Similarity	NPD6673	Approved
0.6932	Remote Similarity	NPD6904	Approved
0.6932	Remote Similarity	NPD6080	Approved
0.6883	Remote Similarity	NPD4137	Phase 3
0.6795	Remote Similarity	NPD4747	Approved
0.6778	Remote Similarity	NPD6050	Approved
0.6757	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5733	Approved
0.675	Remote Similarity	NPD4058	Approved
0.6742	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3704	Approved
0.6709	Remote Similarity	NPD5276	Approved
0.6707	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6627	Remote Similarity	NPD3617	Approved
0.6596	Remote Similarity	NPD6083	Phase 2
0.6596	Remote Similarity	NPD6084	Phase 2
0.6593	Remote Similarity	NPD5694	Approved
0.6593	Remote Similarity	NPD5693	Phase 1
0.6591	Remote Similarity	NPD7334	Approved
0.6591	Remote Similarity	NPD6409	Approved
0.6591	Remote Similarity	NPD5690	Phase 2
0.6591	Remote Similarity	NPD5330	Approved
0.6591	Remote Similarity	NPD7146	Approved
0.6591	Remote Similarity	NPD6098	Approved
0.6591	Remote Similarity	NPD6684	Approved
0.6591	Remote Similarity	NPD5279	Phase 3
0.6591	Remote Similarity	NPD7521	Approved
0.6559	Remote Similarity	NPD5695	Phase 3
0.6556	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD4197	Approved
0.6543	Remote Similarity	NPD4687	Approved
0.6512	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7331	Phase 2
0.6444	Remote Similarity	NPD6903	Approved
0.6444	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD287	Approved
0.6437	Remote Similarity	NPD6110	Phase 1
0.6404	Remote Similarity	NPD5280	Approved
0.6404	Remote Similarity	NPD4694	Approved
0.6383	Remote Similarity	NPD4629	Approved
0.6383	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD3668	Phase 3
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD5696	Approved
0.6353	Remote Similarity	NPD4195	Approved
0.6333	Remote Similarity	NPD3573	Approved
0.6329	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3667	Approved
0.6322	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD4223	Phase 3
0.6316	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD5221	Approved
0.6316	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5282	Discontinued
0.6277	Remote Similarity	NPD7748	Approved
0.6277	Remote Similarity	NPD7900	Approved
0.6277	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5173	Approved
0.6237	Remote Similarity	NPD6079	Approved
0.6237	Remote Similarity	NPD7515	Phase 2
0.6222	Remote Similarity	NPD3618	Phase 1
0.6222	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5654	Approved
0.6211	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8028	Phase 2
0.6196	Remote Similarity	NPD5328	Approved
0.6176	Remote Similarity	NPD6899	Approved
0.6176	Remote Similarity	NPD6881	Approved
0.617	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7341	Phase 2
0.6146	Remote Similarity	NPD4697	Phase 3
0.6146	Remote Similarity	NPD7732	Phase 3
0.6139	Remote Similarity	NPD6675	Approved
0.6139	Remote Similarity	NPD5739	Approved
0.6139	Remote Similarity	NPD7128	Approved
0.6139	Remote Similarity	NPD6402	Approved
0.6122	Remote Similarity	NPD4696	Approved
0.6122	Remote Similarity	NPD5285	Approved
0.6122	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD1696	Phase 3
0.6111	Remote Similarity	NPD1694	Approved
0.6087	Remote Similarity	NPD5208	Approved
0.6082	Remote Similarity	NPD4755	Approved
0.6082	Remote Similarity	NPD7902	Approved
0.6082	Remote Similarity	NPD5959	Approved
0.6078	Remote Similarity	NPD5697	Approved
0.6078	Remote Similarity	NPD6614	Approved
0.6067	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5223	Approved
0.6058	Remote Similarity	NPD7290	Approved
0.6058	Remote Similarity	NPD6883	Approved
0.6058	Remote Similarity	NPD7102	Approved
0.6044	Remote Similarity	NPD4138	Approved
0.6044	Remote Similarity	NPD4693	Phase 3
0.6044	Remote Similarity	NPD5205	Approved
0.6044	Remote Similarity	NPD4689	Approved
0.6044	Remote Similarity	NPD4688	Approved
0.6044	Remote Similarity	NPD4623	Approved
0.6044	Remote Similarity	NPD4690	Approved
0.6044	Remote Similarity	NPD4519	Discontinued
0.6019	Remote Similarity	NPD7320	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5962	Remote Similarity	NPD6013	Approved
0.5962	Remote Similarity	NPD6373	Approved
0.5962	Remote Similarity	NPD6372	Approved
0.5962	Remote Similarity	NPD6014	Approved
0.5962	Remote Similarity	NPD6012	Approved
0.596	Remote Similarity	NPD4700	Approved
0.5957	Remote Similarity	NPD5207	Approved
0.5955	Remote Similarity	NPD5209	Approved
0.5943	Remote Similarity	NPD6882	Approved
0.5943	Remote Similarity	NPD8297	Approved
0.5941	Remote Similarity	NPD5175	Approved
0.5941	Remote Similarity	NPD5174	Approved
0.5922	Remote Similarity	NPD5701	Approved
0.5895	Remote Similarity	NPD5284	Approved
0.5895	Remote Similarity	NPD5281	Approved
0.5889	Remote Similarity	NPD4788	Approved
0.5882	Remote Similarity	NPD8264	Approved
0.5882	Remote Similarity	NPD6942	Approved
0.5882	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD8039	Approved
0.5882	Remote Similarity	NPD7339	Approved
0.5859	Remote Similarity	NPD4225	Approved
0.5854	Remote Similarity	NPD6923	Approved
0.5854	Remote Similarity	NPD6922	Approved
0.5849	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5091	Approved
0.5833	Remote Similarity	NPD4202	Approved
0.5833	Remote Similarity	NPD5133	Approved
0.5823	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7614	Phase 1
0.5814	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD7645	Phase 2
0.5789	Remote Similarity	NPD4096	Approved
0.5789	Remote Similarity	NPD5785	Approved
0.5784	Remote Similarity	NPD4754	Approved
0.5783	Remote Similarity	NPD7143	Approved
0.5783	Remote Similarity	NPD7144	Approved
0.578	Remote Similarity	NPD6868	Approved
0.5773	Remote Similarity	NPD6001	Approved
0.5769	Remote Similarity	NPD4194	Approved
0.5769	Remote Similarity	NPD4193	Approved
0.5769	Remote Similarity	NPD4191	Approved
0.5769	Remote Similarity	NPD4192	Approved
0.5765	Remote Similarity	NPD6924	Approved
0.5765	Remote Similarity	NPD6926	Approved
0.5765	Remote Similarity	NPD4785	Approved
0.5765	Remote Similarity	NPD4784	Approved
0.575	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD4518	Approved
0.5729	Remote Similarity	NPD6411	Approved
0.5729	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD4243	Approved
0.5714	Remote Similarity	NPD7152	Approved
0.5714	Remote Similarity	NPD5168	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD7151	Approved
0.5714	Remote Similarity	NPD7150	Approved
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD4730	Approved
0.57	Remote Similarity	NPD7638	Approved
0.5684	Remote Similarity	NPD6051	Approved
0.5682	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6335	Approved
0.5673	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD4768	Approved
0.5673	Remote Similarity	NPD6008	Approved
0.5644	Remote Similarity	NPD7639	Approved
0.5644	Remote Similarity	NPD7640	Approved
0.5636	Remote Similarity	NPD6274	Approved
0.5632	Remote Similarity	NPD6933	Approved
0.5631	Remote Similarity	NPD6052	Approved
0.5625	Remote Similarity	NPD7101	Approved
0.5625	Remote Similarity	NPD7100	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