NPASS Compound

Structure

NPC196479 OpenBabel07101718292D 22 22 0 0 0 0 0 0 0 0999 V2000 8.6603 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 2.5981 0.5000 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 0.8660 0.5000 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 -0.0000 -1.0000 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 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 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	352.954
LogP:	6.909
LogD:	4.683
LogS:	-3.582
# Rotatable Bonds:	12
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	2.188
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.922
MDCK Permeability:	1.5130272913665976e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	99.95636749267578%
Volume Distribution (VD):	3.614
Pgp-substrate:	0.5457928776741028%

ADMET: Metabolism

CYP1A2-inhibitor:	0.698
CYP1A2-substrate:	0.203
CYP2C19-inhibitor:	0.767
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.283
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	3.743
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.385
Skin Sensitization:	0.962
Carcinogencity:	0.036
Eye Corrosion:	0.948
Eye Irritation:	0.98
Respiratory Toxicity:	0.681

Download Data

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

Natural Product: NPC196479

Natural Product ID:	NPC196479
*Common Name:**	Obliquol B
IUPAC Name:	4-[(E)-tetradec-4-enyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	JUSVGHZRAMJHHC-ZHACJKMWSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-16-19(21)20(22)17-18/h10-11,15-17,21-22H,2-9,12-14H2,1H3/b11-10+
SMILES:	CCCCCCCCC/C=C/CCCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457469
PubChem CID:	25113692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO22658	Piper obliquum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18276144]
NPO22658	Piper obliquum	Species	Piperaceae	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	1
MIC	2

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[501709]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[501709]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	5.0	ug.mL-1	PMID[501709]

☑ 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 NPC196479 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	248
0.1-0.2	1771
0.2-0.3	5943
0.3-0.4	13561
0.4-0.5	5294
0.5-0.6	9215
0.6-0.7	4637
0.7-0.8	1680
0.8-0.85	258
0.85-0.9	74
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC109955
0.9495	High Similarity	NPC477814
0.9368	High Similarity	NPC107522
0.9293	High Similarity	NPC120719
0.9286	High Similarity	NPC110764
0.9216	High Similarity	NPC228343
0.9216	High Similarity	NPC254833
0.91	High Similarity	NPC12278
0.91	High Similarity	NPC471511
0.9082	High Similarity	NPC131587
0.9029	High Similarity	NPC62258
0.9029	High Similarity	NPC55617
0.901	High Similarity	NPC239291
0.899	High Similarity	NPC223393
0.8958	High Similarity	NPC147284
0.8958	High Similarity	NPC3358
0.8958	High Similarity	NPC162314
0.8958	High Similarity	NPC210497
0.8958	High Similarity	NPC94139
0.8958	High Similarity	NPC306884
0.8947	High Similarity	NPC55561
0.8942	High Similarity	NPC147634
0.8942	High Similarity	NPC226401
0.8942	High Similarity	NPC174096
0.8942	High Similarity	NPC79793
0.8942	High Similarity	NPC120982
0.8911	High Similarity	NPC79672
0.8911	High Similarity	NPC52087
0.8857	High Similarity	NPC187583
0.8857	High Similarity	NPC257430
0.8857	High Similarity	NPC297657
0.8857	High Similarity	NPC179002
0.8842	High Similarity	NPC280347
0.8842	High Similarity	NPC177420
0.875	High Similarity	NPC192
0.875	High Similarity	NPC233835
0.8737	High Similarity	NPC27974
0.8737	High Similarity	NPC25493
0.8737	High Similarity	NPC113460
0.87	High Similarity	NPC260775
0.8679	High Similarity	NPC8547
0.8679	High Similarity	NPC173746
0.8679	High Similarity	NPC156840
0.8679	High Similarity	NPC257124
0.8646	High Similarity	NPC242240
0.8646	High Similarity	NPC123273
0.8646	High Similarity	NPC318325
0.8636	High Similarity	NPC203124
0.8632	High Similarity	NPC23167
0.8627	High Similarity	NPC477801
0.8627	High Similarity	NPC477802
0.8614	High Similarity	NPC12931
0.8614	High Similarity	NPC70677
0.8614	High Similarity	NPC248396
0.8614	High Similarity	NPC48730
0.8614	High Similarity	NPC129373
0.8614	High Similarity	NPC130756
0.8611	High Similarity	NPC120280
0.86	High Similarity	NPC152097
0.8586	High Similarity	NPC26244
0.8586	High Similarity	NPC274678
0.8586	High Similarity	NPC32714
0.8585	High Similarity	NPC222084
0.8559	High Similarity	NPC217174
0.8558	High Similarity	NPC1786
0.8558	High Similarity	NPC294902
0.8558	High Similarity	NPC1075
0.8558	High Similarity	NPC19149
0.8545	High Similarity	NPC200988
0.8545	High Similarity	NPC175799
0.8545	High Similarity	NPC164386
0.8545	High Similarity	NPC610
0.8545	High Similarity	NPC145023
0.8526	High Similarity	NPC197783
0.8519	High Similarity	NPC148969
0.8519	High Similarity	NPC264558
0.8505	High Similarity	NPC268032
0.85	High Similarity	NPC473388
0.8491	Intermediate Similarity	NPC7097
0.8491	Intermediate Similarity	NPC36108
0.8491	Intermediate Similarity	NPC246358
0.8491	Intermediate Similarity	NPC233731
0.8485	Intermediate Similarity	NPC27323
0.8485	Intermediate Similarity	NPC76938
0.8485	Intermediate Similarity	NPC316301
0.8485	Intermediate Similarity	NPC151715
0.8482	Intermediate Similarity	NPC475245
0.8476	Intermediate Similarity	NPC176527
0.8469	Intermediate Similarity	NPC270547
0.8469	Intermediate Similarity	NPC304541
0.8468	Intermediate Similarity	NPC86198
0.8468	Intermediate Similarity	NPC309434
0.8468	Intermediate Similarity	NPC470626
0.8468	Intermediate Similarity	NPC144343
0.8455	Intermediate Similarity	NPC299252
0.8455	Intermediate Similarity	NPC61062
0.8455	Intermediate Similarity	NPC277394
0.8454	Intermediate Similarity	NPC258219
0.8454	Intermediate Similarity	NPC98772
0.8447	Intermediate Similarity	NPC302219
0.8447	Intermediate Similarity	NPC222522
0.8447	Intermediate Similarity	NPC85479
0.8447	Intermediate Similarity	NPC146798
0.8447	Intermediate Similarity	NPC168303
0.8447	Intermediate Similarity	NPC53051
0.8447	Intermediate Similarity	NPC249828
0.8447	Intermediate Similarity	NPC94351
0.8447	Intermediate Similarity	NPC24404
0.8447	Intermediate Similarity	NPC313030
0.8447	Intermediate Similarity	NPC106396
0.8447	Intermediate Similarity	NPC71002
0.8447	Intermediate Similarity	NPC242342
0.844	Intermediate Similarity	NPC142599
0.8438	Intermediate Similarity	NPC184169
0.8431	Intermediate Similarity	NPC166761
0.8426	Intermediate Similarity	NPC146422
0.8426	Intermediate Similarity	NPC51698
0.8426	Intermediate Similarity	NPC471179
0.8421	Intermediate Similarity	NPC175313
0.8421	Intermediate Similarity	NPC150837
0.8421	Intermediate Similarity	NPC248817
0.8416	Intermediate Similarity	NPC474073
0.8416	Intermediate Similarity	NPC475078
0.8407	Intermediate Similarity	NPC24125
0.8396	Intermediate Similarity	NPC114392
0.8396	Intermediate Similarity	NPC58427
0.8396	Intermediate Similarity	NPC105727
0.8396	Intermediate Similarity	NPC34864
0.8393	Intermediate Similarity	NPC311595
0.8393	Intermediate Similarity	NPC470214
0.8393	Intermediate Similarity	NPC109371
0.8393	Intermediate Similarity	NPC24474
0.8393	Intermediate Similarity	NPC470215
0.8393	Intermediate Similarity	NPC310338
0.8393	Intermediate Similarity	NPC70084
0.8393	Intermediate Similarity	NPC281298
0.8384	Intermediate Similarity	NPC55903
0.8384	Intermediate Similarity	NPC138117
0.8384	Intermediate Similarity	NPC325292
0.8378	Intermediate Similarity	NPC277588
0.8378	Intermediate Similarity	NPC293619
0.8378	Intermediate Similarity	NPC86947
0.8378	Intermediate Similarity	NPC16030
0.8367	Intermediate Similarity	NPC300017
0.835	Intermediate Similarity	NPC24407
0.835	Intermediate Similarity	NPC101025
0.835	Intermediate Similarity	NPC72947
0.835	Intermediate Similarity	NPC192032
0.835	Intermediate Similarity	NPC284011
0.835	Intermediate Similarity	NPC471578
0.835	Intermediate Similarity	NPC252105
0.835	Intermediate Similarity	NPC11280
0.835	Intermediate Similarity	NPC294186
0.835	Intermediate Similarity	NPC477685
0.835	Intermediate Similarity	NPC147310
0.835	Intermediate Similarity	NPC166313
0.835	Intermediate Similarity	NPC137415
0.835	Intermediate Similarity	NPC80800
0.8349	Intermediate Similarity	NPC471485
0.8333	Intermediate Similarity	NPC139617
0.8333	Intermediate Similarity	NPC78918
0.8333	Intermediate Similarity	NPC195873
0.8333	Intermediate Similarity	NPC226250
0.8333	Intermediate Similarity	NPC237667
0.8333	Intermediate Similarity	NPC92730
0.8319	Intermediate Similarity	NPC117780
0.8319	Intermediate Similarity	NPC56214
0.8319	Intermediate Similarity	NPC227217
0.8319	Intermediate Similarity	NPC95614
0.8319	Intermediate Similarity	NPC165133
0.8319	Intermediate Similarity	NPC232316
0.8319	Intermediate Similarity	NPC242885
0.8317	Intermediate Similarity	NPC202986
0.8317	Intermediate Similarity	NPC82664
0.8317	Intermediate Similarity	NPC216520
0.8317	Intermediate Similarity	NPC132271
0.8317	Intermediate Similarity	NPC292730
0.8316	Intermediate Similarity	NPC265146
0.8316	Intermediate Similarity	NPC124436
0.83	Intermediate Similarity	NPC245187
0.8288	Intermediate Similarity	NPC221049
0.8288	Intermediate Similarity	NPC281277
0.8283	Intermediate Similarity	NPC231150
0.8283	Intermediate Similarity	NPC45040
0.8283	Intermediate Similarity	NPC155908
0.8273	Intermediate Similarity	NPC261453
0.8273	Intermediate Similarity	NPC33749
0.8273	Intermediate Similarity	NPC328593
0.8269	Intermediate Similarity	NPC108497
0.8252	Intermediate Similarity	NPC72729
0.8252	Intermediate Similarity	NPC211885
0.8252	Intermediate Similarity	NPC294741
0.8252	Intermediate Similarity	NPC225506
0.8252	Intermediate Similarity	NPC10588
0.8247	Intermediate Similarity	NPC407
0.8247	Intermediate Similarity	NPC307235
0.8246	Intermediate Similarity	NPC98305
0.8246	Intermediate Similarity	NPC470848
0.8246	Intermediate Similarity	NPC207613
0.8246	Intermediate Similarity	NPC470849

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 NPC196479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	1064
0.2-0.3	1549
0.3-0.4	2942
0.4-0.5	1794
0.5-0.6	1067
0.6-0.7	381
0.7-0.8	89
0.8-0.85	9
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9216	High Similarity	NPD3022	Approved
0.9216	High Similarity	NPD3021	Approved
0.8679	High Similarity	NPD228	Approved
0.8673	High Similarity	NPD2933	Approved
0.8673	High Similarity	NPD2934	Approved
0.8586	High Similarity	NPD2860	Approved
0.8586	High Similarity	NPD2859	Approved
0.8515	High Similarity	NPD3020	Approved
0.8485	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8426	Intermediate Similarity	NPD9377	Approved
0.8426	Intermediate Similarity	NPD9379	Approved
0.84	Intermediate Similarity	NPD844	Approved
0.8316	Intermediate Similarity	NPD111	Approved
0.8137	Intermediate Similarity	NPD288	Approved
0.8077	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD940	Approved
0.8	Intermediate Similarity	NPD846	Approved
0.7966	Intermediate Similarity	NPD5311	Approved
0.7966	Intermediate Similarity	NPD5310	Approved
0.7905	Intermediate Similarity	NPD1242	Phase 1
0.7899	Intermediate Similarity	NPD3053	Approved
0.7899	Intermediate Similarity	NPD3055	Approved
0.7864	Intermediate Similarity	NPD1809	Phase 2
0.7845	Intermediate Similarity	NPD9384	Approved
0.7845	Intermediate Similarity	NPD9381	Approved
0.7843	Intermediate Similarity	NPD845	Approved
0.7731	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD9622	Approved
0.7706	Intermediate Similarity	NPD1444	Approved
0.7706	Intermediate Similarity	NPD1445	Approved
0.7699	Intermediate Similarity	NPD5283	Phase 1
0.7667	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4750	Phase 3
0.7642	Intermediate Similarity	NPD3027	Phase 3
0.7611	Intermediate Similarity	NPD7635	Approved
0.757	Intermediate Similarity	NPD3028	Approved
0.7568	Intermediate Similarity	NPD2684	Approved
0.7565	Intermediate Similarity	NPD6671	Approved
0.7563	Intermediate Similarity	NPD3092	Approved
0.7544	Intermediate Similarity	NPD2229	Approved
0.7544	Intermediate Similarity	NPD2228	Approved
0.7544	Intermediate Similarity	NPD2234	Approved
0.7541	Intermediate Similarity	NPD9619	Approved
0.7541	Intermediate Similarity	NPD9620	Approved
0.7541	Intermediate Similarity	NPD257	Approved
0.7541	Intermediate Similarity	NPD9621	Approved
0.7541	Intermediate Similarity	NPD258	Approved
0.7523	Intermediate Similarity	NPD9610	Approved
0.7523	Intermediate Similarity	NPD9608	Approved
0.7521	Intermediate Similarity	NPD3091	Approved
0.752	Intermediate Similarity	NPD2674	Phase 3
0.75	Intermediate Similarity	NPD1792	Phase 2
0.75	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1357	Approved
0.7456	Intermediate Similarity	NPD7843	Approved
0.744	Intermediate Similarity	NPD597	Approved
0.744	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD601	Approved
0.744	Intermediate Similarity	NPD598	Approved
0.7414	Intermediate Similarity	NPD7157	Approved
0.7395	Intermediate Similarity	NPD2932	Approved
0.7395	Intermediate Similarity	NPD4059	Approved
0.7395	Intermediate Similarity	NPD3019	Approved
0.7381	Intermediate Similarity	NPD1136	Approved
0.7381	Intermediate Similarity	NPD1130	Approved
0.7381	Intermediate Similarity	NPD1132	Approved
0.7368	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD9094	Approved
0.7344	Intermediate Similarity	NPD5314	Approved
0.7339	Intermediate Similarity	NPD9569	Approved
0.7323	Intermediate Similarity	NPD3059	Approved
0.7323	Intermediate Similarity	NPD3062	Approved
0.7323	Intermediate Similarity	NPD3061	Approved
0.7323	Intermediate Similarity	NPD3620	Phase 2
0.7323	Intermediate Similarity	NPD825	Approved
0.7323	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD826	Approved
0.7321	Intermediate Similarity	NPD2342	Discontinued
0.7317	Intermediate Similarity	NPD3094	Phase 2
0.7311	Intermediate Similarity	NPD4093	Discontinued
0.7302	Intermediate Similarity	NPD3145	Approved
0.7302	Intermediate Similarity	NPD3144	Approved
0.728	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9500	Approved
0.7264	Intermediate Similarity	NPD9296	Approved
0.7252	Intermediate Similarity	NPD7266	Discontinued
0.7244	Intermediate Similarity	NPD259	Phase 1
0.7241	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9494	Approved
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1558	Phase 1
0.7179	Intermediate Similarity	NPD1793	Approved
0.7179	Intermediate Similarity	NPD9618	Approved
0.7179	Intermediate Similarity	NPD1791	Approved
0.7179	Intermediate Similarity	NPD9614	Approved
0.7158	Intermediate Similarity	NPD9087	Approved
0.7154	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7132	Intermediate Similarity	NPD275	Approved
0.7132	Intermediate Similarity	NPD555	Phase 2
0.7132	Intermediate Similarity	NPD274	Approved
0.7131	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1751	Approved
0.7107	Intermediate Similarity	NPD3095	Discontinued
0.7107	Intermediate Similarity	NPD4626	Approved
0.7107	Intermediate Similarity	NPD2286	Discontinued
0.709	Intermediate Similarity	NPD8166	Discontinued
0.7087	Intermediate Similarity	NPD9536	Phase 1
0.7087	Intermediate Similarity	NPD9537	Phase 1
0.7083	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD817	Approved
0.7077	Intermediate Similarity	NPD823	Approved
0.7073	Intermediate Similarity	NPD9269	Phase 2
0.7064	Intermediate Similarity	NPD9273	Approved
0.7063	Intermediate Similarity	NPD5736	Approved
0.7054	Intermediate Similarity	NPD943	Approved
0.7054	Intermediate Similarity	NPD1613	Approved
0.7054	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD9088	Approved
0.704	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD290	Approved
0.7009	Intermediate Similarity	NPD821	Approved
0.7	Intermediate Similarity	NPD856	Approved
0.7	Intermediate Similarity	NPD9615	Approved
0.7	Intermediate Similarity	NPD9616	Approved
0.7	Intermediate Similarity	NPD9613	Approved
0.7	Intermediate Similarity	NPD16	Approved
0.6992	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3705	Approved
0.6984	Remote Similarity	NPD6584	Phase 3
0.6975	Remote Similarity	NPD256	Approved
0.6975	Remote Similarity	NPD255	Approved
0.6967	Remote Similarity	NPD4589	Approved
0.6967	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7095	Approved
0.6942	Remote Similarity	NPD5304	Approved
0.6942	Remote Similarity	NPD5303	Approved
0.6942	Remote Similarity	NPD316	Approved
0.6939	Remote Similarity	NPD9294	Approved
0.693	Remote Similarity	NPD968	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6897	Remote Similarity	NPD5451	Approved
0.6891	Remote Similarity	NPD475	Phase 2
0.688	Remote Similarity	NPD2982	Phase 2
0.688	Remote Similarity	NPD2983	Phase 2
0.6875	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.687	Remote Similarity	NPD230	Phase 1
0.686	Remote Similarity	NPD317	Approved
0.686	Remote Similarity	NPD318	Approved
0.685	Remote Similarity	NPD2194	Approved
0.685	Remote Similarity	NPD2195	Approved
0.6846	Remote Similarity	NPD6663	Approved
0.6842	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2667	Approved
0.6829	Remote Similarity	NPD2668	Approved
0.6812	Remote Similarity	NPD2420	Approved
0.6812	Remote Similarity	NPD2421	Approved
0.68	Remote Similarity	NPD2233	Approved
0.68	Remote Similarity	NPD2230	Approved
0.68	Remote Similarity	NPD2562	Approved
0.68	Remote Similarity	NPD2981	Phase 2
0.68	Remote Similarity	NPD2232	Approved
0.68	Remote Similarity	NPD2561	Approved
0.6797	Remote Similarity	NPD3637	Approved
0.6797	Remote Similarity	NPD2861	Phase 2
0.6797	Remote Similarity	NPD3018	Phase 2
0.6797	Remote Similarity	NPD3636	Approved
0.6797	Remote Similarity	NPD3635	Approved
0.6791	Remote Similarity	NPD9570	Approved
0.6791	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3134	Approved
0.6777	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD9568	Approved
0.6777	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3496	Discontinued
0.6774	Remote Similarity	NPD3023	Approved
0.6774	Remote Similarity	NPD3026	Approved
0.6774	Remote Similarity	NPD3421	Phase 3
0.6769	Remote Similarity	NPD5718	Phase 2
0.6765	Remote Similarity	NPD3060	Approved
0.6765	Remote Similarity	NPD9089	Approved
0.6748	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5691	Approved
0.6748	Remote Similarity	NPD3025	Approved
0.6748	Remote Similarity	NPD9268	Approved
0.6748	Remote Similarity	NPD3024	Approved
0.6746	Remote Similarity	NPD4749	Approved
0.6746	Remote Similarity	NPD1755	Approved
0.6746	Remote Similarity	NPD4659	Approved
0.6746	Remote Similarity	NPD6582	Phase 2
0.6746	Remote Similarity	NPD6583	Phase 3
0.6744	Remote Similarity	NPD2606	Approved
0.6744	Remote Similarity	NPD2605	Approved
0.6742	Remote Similarity	NPD5735	Approved
0.6739	Remote Similarity	NPD3845	Phase 1

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