NPASS Compound

Structure

NPC99308 OpenBabel07101718202D 26 28 0 0 1 0 0 0 0 0999 V2000 4.9641 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 3.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 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 3.2321 2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 1 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 23 2 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 21 1 1 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 3 1 1 0 0 0 22 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	3.847
LogD:	3.264
LogS:	-4.527
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.436
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.762
MDCK Permeability:	2.7388105081627145e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.82
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	93.8708267211914%
Volume Distribution (VD):	1.002
Pgp-substrate:	3.7009694576263428%

ADMET: Metabolism

CYP1A2-inhibitor:	0.781
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.38
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	2.107
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.947
Carcinogencity:	0.892
Eye Corrosion:	0.047
Eye Irritation:	0.062
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC99308

Natural Product ID:	NPC99308
*Common Name:**	6'-Hydroxy-4'-Methoxyavarone
IUPAC Name:	2-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-3-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	ZEMBAQORKKQPSC-YVUMSICPSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-16(23)11-17(26-5)20(25)19(15)24/h7,11,14,18,24H,6,8-10,12H2,1-5H3/t14-,18+,21+,22+/m0/s1
SMILES:	COC1=CC(=O)C(=C(C1=O)O)C[C@]1(C)[C@@H](C)CC[C@]2([C@H]1CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465323
PubChem CID:	452333
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
NPO33143	Dysidea cinerea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1710654]
NPO33143	Dysidea cinerea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31532203]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	20.0	ug.mL-1	PMID[539160]

☑ 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 NPC99308 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	1353
0.2-0.3	6330
0.3-0.4	15422
0.4-0.5	10314
0.5-0.6	6386
0.6-0.7	2414
0.7-0.8	279
0.8-0.85	13
0.85-0.9	11
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC263997
0.925	High Similarity	NPC132228
0.925	High Similarity	NPC8518
0.9079	High Similarity	NPC1254
0.9012	High Similarity	NPC241512
0.9012	High Similarity	NPC6185
0.8831	High Similarity	NPC26504
0.875	High Similarity	NPC475833
0.875	High Similarity	NPC474085
0.875	High Similarity	NPC55869
0.8734	High Similarity	NPC27817
0.8625	High Similarity	NPC108955
0.8571	High Similarity	NPC147438
0.8415	Intermediate Similarity	NPC103486
0.8354	Intermediate Similarity	NPC110725
0.8333	Intermediate Similarity	NPC474680
0.8333	Intermediate Similarity	NPC133652
0.8293	Intermediate Similarity	NPC470034
0.8293	Intermediate Similarity	NPC475863
0.8276	Intermediate Similarity	NPC475823
0.8276	Intermediate Similarity	NPC474209
0.8171	Intermediate Similarity	NPC287063
0.8158	Intermediate Similarity	NPC188292
0.8158	Intermediate Similarity	NPC260474
0.8148	Intermediate Similarity	NPC189485
0.8148	Intermediate Similarity	NPC30321
0.8125	Intermediate Similarity	NPC92080
0.8118	Intermediate Similarity	NPC255174
0.8118	Intermediate Similarity	NPC33881
0.8095	Intermediate Similarity	NPC105803
0.8077	Intermediate Similarity	NPC474539
0.8072	Intermediate Similarity	NPC116797
0.8072	Intermediate Similarity	NPC225515
0.7922	Intermediate Similarity	NPC310992
0.7922	Intermediate Similarity	NPC87141
0.7907	Intermediate Similarity	NPC32037
0.7889	Intermediate Similarity	NPC263780
0.7882	Intermediate Similarity	NPC53733
0.7865	Intermediate Similarity	NPC223093
0.7841	Intermediate Similarity	NPC53454
0.7831	Intermediate Similarity	NPC475681
0.7821	Intermediate Similarity	NPC474060
0.7816	Intermediate Similarity	NPC94666
0.7802	Intermediate Similarity	NPC23170
0.7778	Intermediate Similarity	NPC175079
0.7778	Intermediate Similarity	NPC26865
0.7778	Intermediate Similarity	NPC174167
0.7778	Intermediate Similarity	NPC470036
0.7763	Intermediate Similarity	NPC251118
0.7738	Intermediate Similarity	NPC2482
0.7722	Intermediate Similarity	NPC251929
0.7722	Intermediate Similarity	NPC2634
0.7722	Intermediate Similarity	NPC265782
0.7711	Intermediate Similarity	NPC74410
0.7701	Intermediate Similarity	NPC472931
0.7701	Intermediate Similarity	NPC90287
0.7701	Intermediate Similarity	NPC33663
0.7701	Intermediate Similarity	NPC472940
0.7692	Intermediate Similarity	NPC155198
0.7683	Intermediate Similarity	NPC180886
0.7683	Intermediate Similarity	NPC470525
0.7683	Intermediate Similarity	NPC112680
0.7683	Intermediate Similarity	NPC292589
0.7647	Intermediate Similarity	NPC121984
0.7647	Intermediate Similarity	NPC278459
0.764	Intermediate Similarity	NPC307298
0.7625	Intermediate Similarity	NPC54123
0.7619	Intermediate Similarity	NPC472490
0.7619	Intermediate Similarity	NPC192329
0.7595	Intermediate Similarity	NPC139397
0.7595	Intermediate Similarity	NPC256846
0.759	Intermediate Similarity	NPC283087
0.7586	Intermediate Similarity	NPC237712
0.7582	Intermediate Similarity	NPC99380
0.7561	Intermediate Similarity	NPC476346
0.7558	Intermediate Similarity	NPC142253
0.7558	Intermediate Similarity	NPC3511
0.7556	Intermediate Similarity	NPC112454
0.7556	Intermediate Similarity	NPC68148
0.7556	Intermediate Similarity	NPC326627
0.7556	Intermediate Similarity	NPC310010
0.7556	Intermediate Similarity	NPC65615
0.7531	Intermediate Similarity	NPC470044
0.7531	Intermediate Similarity	NPC470045
0.7531	Intermediate Similarity	NPC109576
0.7531	Intermediate Similarity	NPC180015
0.7531	Intermediate Similarity	NPC303613
0.7531	Intermediate Similarity	NPC56747
0.7531	Intermediate Similarity	NPC130016
0.7531	Intermediate Similarity	NPC474228
0.7529	Intermediate Similarity	NPC472478
0.7529	Intermediate Similarity	NPC476809
0.7528	Intermediate Similarity	NPC470523
0.7528	Intermediate Similarity	NPC220930
0.7528	Intermediate Similarity	NPC272039
0.7527	Intermediate Similarity	NPC777
0.7527	Intermediate Similarity	NPC147232
0.7526	Intermediate Similarity	NPC179208
0.75	Intermediate Similarity	NPC307176
0.75	Intermediate Similarity	NPC23778
0.75	Intermediate Similarity	NPC469993
0.75	Intermediate Similarity	NPC288253
0.75	Intermediate Similarity	NPC476808
0.75	Intermediate Similarity	NPC469996
0.75	Intermediate Similarity	NPC8571
0.75	Intermediate Similarity	NPC211230
0.75	Intermediate Similarity	NPC260040
0.7473	Intermediate Similarity	NPC129913
0.7473	Intermediate Similarity	NPC113393
0.7471	Intermediate Similarity	NPC470015
0.7471	Intermediate Similarity	NPC49019
0.7471	Intermediate Similarity	NPC41539
0.7471	Intermediate Similarity	NPC168188
0.7467	Intermediate Similarity	NPC127582
0.7444	Intermediate Similarity	NPC470524
0.7442	Intermediate Similarity	NPC189237
0.7442	Intermediate Similarity	NPC472684
0.7442	Intermediate Similarity	NPC44963
0.7439	Intermediate Similarity	NPC128346
0.7439	Intermediate Similarity	NPC219232
0.7439	Intermediate Similarity	NPC264178
0.7419	Intermediate Similarity	NPC474882
0.7419	Intermediate Similarity	NPC474328
0.7416	Intermediate Similarity	NPC203795
0.7416	Intermediate Similarity	NPC327115
0.7416	Intermediate Similarity	NPC475022
0.7416	Intermediate Similarity	NPC118648
0.7416	Intermediate Similarity	NPC472974
0.7416	Intermediate Similarity	NPC222613
0.7412	Intermediate Similarity	NPC90965
0.7412	Intermediate Similarity	NPC170793
0.7412	Intermediate Similarity	NPC476177
0.7407	Intermediate Similarity	NPC474562
0.7407	Intermediate Similarity	NPC190035
0.7403	Intermediate Similarity	NPC475124
0.7403	Intermediate Similarity	NPC469662
0.7403	Intermediate Similarity	NPC285371
0.7396	Intermediate Similarity	NPC474720
0.7386	Intermediate Similarity	NPC144258
0.7386	Intermediate Similarity	NPC473246
0.7386	Intermediate Similarity	NPC87552
0.7381	Intermediate Similarity	NPC472300
0.7381	Intermediate Similarity	NPC476811
0.7381	Intermediate Similarity	NPC165711
0.7375	Intermediate Similarity	NPC262673
0.7363	Intermediate Similarity	NPC31985
0.7363	Intermediate Similarity	NPC1015
0.7363	Intermediate Similarity	NPC474918
0.7363	Intermediate Similarity	NPC477973
0.7356	Intermediate Similarity	NPC311092
0.7356	Intermediate Similarity	NPC472239
0.7356	Intermediate Similarity	NPC321289
0.7356	Intermediate Similarity	NPC327969
0.7356	Intermediate Similarity	NPC472867
0.7349	Intermediate Similarity	NPC65650
0.7347	Intermediate Similarity	NPC111323
0.7342	Intermediate Similarity	NPC4370
0.7342	Intermediate Similarity	NPC243272
0.7342	Intermediate Similarity	NPC290350
0.734	Intermediate Similarity	NPC295347
0.7333	Intermediate Similarity	NPC472304
0.7333	Intermediate Similarity	NPC230016
0.7333	Intermediate Similarity	NPC276764
0.7326	Intermediate Similarity	NPC18955
0.7326	Intermediate Similarity	NPC26139
0.7317	Intermediate Similarity	NPC251705
0.7312	Intermediate Similarity	NPC233118
0.7312	Intermediate Similarity	NPC271652
0.7303	Intermediate Similarity	NPC94531
0.7303	Intermediate Similarity	NPC474537
0.7303	Intermediate Similarity	NPC11711
0.7303	Intermediate Similarity	NPC476426
0.7303	Intermediate Similarity	NPC311702
0.7303	Intermediate Similarity	NPC469948
0.7303	Intermediate Similarity	NPC123319
0.7294	Intermediate Similarity	NPC471409
0.7294	Intermediate Similarity	NPC478247
0.7294	Intermediate Similarity	NPC115515
0.7294	Intermediate Similarity	NPC82635
0.7294	Intermediate Similarity	NPC475994
0.7294	Intermediate Similarity	NPC275494
0.7294	Intermediate Similarity	NPC321514
0.7294	Intermediate Similarity	NPC62336
0.7294	Intermediate Similarity	NPC478246
0.7292	Intermediate Similarity	NPC147954
0.7284	Intermediate Similarity	NPC159577
0.7284	Intermediate Similarity	NPC291062
0.7284	Intermediate Similarity	NPC282593
0.7284	Intermediate Similarity	NPC35734
0.7284	Intermediate Similarity	NPC94743
0.7283	Intermediate Similarity	NPC38952
0.7273	Intermediate Similarity	NPC8091
0.7273	Intermediate Similarity	NPC202118
0.7273	Intermediate Similarity	NPC197238
0.7273	Intermediate Similarity	NPC40170
0.7263	Intermediate Similarity	NPC272411
0.7262	Intermediate Similarity	NPC19907
0.7262	Intermediate Similarity	NPC263582
0.7262	Intermediate Similarity	NPC69408
0.7253	Intermediate Similarity	NPC478259

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 NPC99308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1739
0.2-0.3	4373
0.3-0.4	2096
0.4-0.5	445
0.5-0.6	165
0.6-0.7	152
0.7-0.8	21
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
0.8395	Intermediate Similarity	NPD4695	Discontinued
0.7722	Intermediate Similarity	NPD4691	Approved
0.7717	Intermediate Similarity	NPD5695	Phase 3
0.7614	Intermediate Similarity	NPD5690	Phase 2
0.7595	Intermediate Similarity	NPD4137	Phase 3
0.7556	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4747	Approved
0.75	Intermediate Similarity	NPD3617	Approved
0.7439	Intermediate Similarity	NPD5733	Approved
0.7439	Intermediate Similarity	NPD4687	Approved
0.7439	Intermediate Similarity	NPD4058	Approved
0.7416	Intermediate Similarity	NPD5279	Phase 3
0.7416	Intermediate Similarity	NPD5280	Approved
0.7416	Intermediate Similarity	NPD4694	Approved
0.7407	Intermediate Similarity	NPD5276	Approved
0.7386	Intermediate Similarity	NPD4197	Approved
0.7368	Intermediate Similarity	NPD6083	Phase 2
0.7368	Intermediate Similarity	NPD6084	Phase 2
0.734	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD4629	Approved
0.7303	Intermediate Similarity	NPD5329	Approved
0.7292	Intermediate Similarity	NPD5696	Approved
0.7253	Intermediate Similarity	NPD5737	Approved
0.7253	Intermediate Similarity	NPD6672	Approved
0.7191	Intermediate Similarity	NPD3133	Approved
0.7191	Intermediate Similarity	NPD3665	Phase 1
0.7191	Intermediate Similarity	NPD3666	Approved
0.7159	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD3667	Approved
0.7159	Intermediate Similarity	NPD4221	Approved
0.7126	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5692	Phase 3
0.7083	Intermediate Similarity	NPD5221	Approved
0.7083	Intermediate Similarity	NPD5222	Approved
0.7083	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD5286	Approved
0.7041	Intermediate Similarity	NPD4696	Approved
0.7037	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3618	Phase 1
0.7021	Intermediate Similarity	NPD6050	Approved
0.7021	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD4755	Approved
0.701	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.6989	Remote Similarity	NPD6904	Approved
0.6989	Remote Similarity	NPD6080	Approved
0.6989	Remote Similarity	NPD6673	Approved
0.6961	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD4697	Phase 3
0.69	Remote Similarity	NPD5225	Approved
0.69	Remote Similarity	NPD5226	Approved
0.69	Remote Similarity	NPD5224	Approved
0.69	Remote Similarity	NPD4633	Approved
0.69	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6889	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7748	Approved
0.6869	Remote Similarity	NPD4700	Approved
0.6863	Remote Similarity	NPD6675	Approved
0.6863	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD5739	Approved
0.6854	Remote Similarity	NPD8028	Phase 2
0.6848	Remote Similarity	NPD4623	Approved
0.6848	Remote Similarity	NPD5205	Approved
0.6848	Remote Similarity	NPD4690	Approved
0.6848	Remote Similarity	NPD4138	Approved
0.6848	Remote Similarity	NPD4689	Approved
0.6848	Remote Similarity	NPD4519	Discontinued
0.6848	Remote Similarity	NPD4693	Phase 3
0.6848	Remote Similarity	NPD4688	Approved
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD5693	Phase 1
0.6842	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD7515	Phase 2
0.6842	Remote Similarity	NPD5281	Approved
0.6835	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5174	Approved
0.6832	Remote Similarity	NPD5175	Approved
0.6827	Remote Similarity	NPD6012	Approved
0.6827	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD6014	Approved
0.6813	Remote Similarity	NPD3668	Phase 3
0.6809	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD5223	Approved
0.6796	Remote Similarity	NPD5701	Approved
0.679	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3704	Approved
0.6782	Remote Similarity	NPD4756	Discovery
0.6771	Remote Similarity	NPD6399	Phase 3
0.6771	Remote Similarity	NPD5133	Approved
0.6765	Remote Similarity	NPD5141	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6753	Remote Similarity	NPD287	Approved
0.6731	Remote Similarity	NPD6011	Approved
0.6731	Remote Similarity	NPD7320	Approved
0.6701	Remote Similarity	NPD5282	Discontinued
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6633	Remote Similarity	NPD5654	Approved
0.6629	Remote Similarity	NPD4195	Approved
0.6598	Remote Similarity	NPD4202	Approved
0.6596	Remote Similarity	NPD3573	Approved
0.6571	Remote Similarity	NPD4730	Approved
0.6571	Remote Similarity	NPD5128	Approved
0.6571	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD5091	Approved
0.6566	Remote Similarity	NPD7614	Phase 1
0.6562	Remote Similarity	NPD4096	Approved
0.6538	Remote Similarity	NPD4768	Approved
0.6538	Remote Similarity	NPD4767	Approved
0.6526	Remote Similarity	NPD4518	Approved
0.6526	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6903	Approved
0.6522	Remote Similarity	NPD4788	Approved
0.6505	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD5959	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6484	Remote Similarity	NPD4139	Approved
0.6484	Remote Similarity	NPD4692	Approved
0.6455	Remote Similarity	NPD6274	Approved
0.6449	Remote Similarity	NPD5249	Phase 3
0.6449	Remote Similarity	NPD4634	Approved
0.6449	Remote Similarity	NPD5250	Approved
0.6449	Remote Similarity	NPD5251	Approved
0.6449	Remote Similarity	NPD5247	Approved
0.6449	Remote Similarity	NPD5248	Approved
0.6415	Remote Similarity	NPD5168	Approved
0.6413	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7732	Phase 3
0.6392	Remote Similarity	NPD5207	Approved
0.6389	Remote Similarity	NPD5217	Approved
0.6389	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5215	Approved
0.6389	Remote Similarity	NPD5216	Approved
0.6386	Remote Similarity	NPD7331	Phase 2
0.6383	Remote Similarity	NPD1696	Phase 3
0.6364	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7900	Approved
0.6354	Remote Similarity	NPD5208	Approved
0.6321	Remote Similarity	NPD6412	Phase 2
0.6306	Remote Similarity	NPD6868	Approved
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5135	Approved
0.6296	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5169	Approved
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6101	Approved
0.6283	Remote Similarity	NPD7100	Approved
0.6283	Remote Similarity	NPD7101	Approved
0.6273	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD5127	Approved
0.6228	Remote Similarity	NPD6319	Approved
0.6228	Remote Similarity	NPD6054	Approved
0.6203	Remote Similarity	NPD8779	Phase 3
0.6195	Remote Similarity	NPD6335	Approved
0.6195	Remote Similarity	NPD6314	Approved
0.6195	Remote Similarity	NPD6313	Approved
0.6174	Remote Similarity	NPD6016	Approved
0.6174	Remote Similarity	NPD6015	Approved
0.617	Remote Similarity	NPD6110	Phase 1
0.6168	Remote Similarity	NPD6614	Approved
0.6121	Remote Similarity	NPD6370	Approved
0.6121	Remote Similarity	NPD5988	Approved
0.6111	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7115	Discovery
0.6087	Remote Similarity	NPD7645	Phase 2
0.6087	Remote Similarity	NPD6059	Approved
0.6071	Remote Similarity	NPD5167	Approved
0.6071	Remote Similarity	NPD7341	Phase 2
0.6058	Remote Similarity	NPD6404	Discontinued
0.6042	Remote Similarity	NPD1694	Approved
0.604	Remote Similarity	NPD6001	Approved
0.6034	Remote Similarity	NPD6909	Approved
0.6034	Remote Similarity	NPD6908	Approved
0.6034	Remote Similarity	NPD5983	Phase 2

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