NPASS Compound

Structure

CID140233 OpenBabel06191715502D 21 23 0 0 1 0 0 0 0 0999 V2000 3.8434 -0.1925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2964 -0.9949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3115 -4.2981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9213 -2.4175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7426 -0.3550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3480 -2.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4391 -1.8101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1500 -3.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2814 -2.7199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5678 -1.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0813 -3.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5815 -3.3746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 -0.5248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3383 -1.0131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2444 -3.5174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8750 -1.8520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9240 -1.9703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7426 -2.9114 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8299 -0.4792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 16 14 1 1 0 0 0 16 17 1 0 0 0 0 17 19 1 1 0 0 0 18 20 1 6 0 0 0 18 21 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 6 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	6.118
LogD:	4.666
LogS:	-5.765
# Rotatable Bonds:	1
TPSA:	12.53
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.833
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.567
MDCK Permeability:	1.595056164660491e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.491
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	93.8071517944336%
Volume Distribution (VD):	2.214
Pgp-substrate:	3.7090952396392822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.203
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.239
CYP2D6-inhibitor:	0.114
CYP2D6-substrate:	0.71
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.391

ADMET: Excretion

Clearance (CL):	8.836
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.428
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.2
Skin Sensitization:	0.959
Carcinogencity:	0.312
Eye Corrosion:	0.988
Eye Irritation:	0.94
Respiratory Toxicity:	0.516

Download Data

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

Natural Product: NPC140233

Natural Product ID:	NPC140233
*Common Name:**	QYPBSHVQNJCZQA-SJCKPFSWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QYPBSHVQNJCZQA-SJCKPFSWSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14(2)16-9-12-19(4)11-8-15(3)6-7-18-20(5,21-18)13-10-17(16)19/h8,16-18H,1,6-7,9-13H2,2-5H3/b15-8+/t16-,17+,18+,19+,20+/m1/s1
SMILES:	C/C/1=CC[C@@]2(C)CC[C@@H]([C@@H]2CC[C@]2([C@H](CC1)O2)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689082
PubChem CID:	51040057
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

*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
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	at a depth of 0.1-1 m, Elafonissos Island (3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	Elafonissos Island (GPS coordinates 3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29308	Mycobacterium marinum	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29313	Halomonas meridiana	Species	Halomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[448223]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[448223]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[448223]

☑ 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 NPC140233 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	226
0.1-0.2	2537
0.2-0.3	15878
0.3-0.4	10614
0.4-0.5	7764
0.5-0.6	4801
0.6-0.7	785
0.7-0.8	77
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC287744
0.8644	High Similarity	NPC223604
0.8529	High Similarity	NPC107783
0.8529	High Similarity	NPC92909
0.8387	Intermediate Similarity	NPC5698
0.8358	Intermediate Similarity	NPC22301
0.831	Intermediate Similarity	NPC186109
0.8308	Intermediate Similarity	NPC477009
0.8308	Intermediate Similarity	NPC238352
0.8254	Intermediate Similarity	NPC323153
0.8169	Intermediate Similarity	NPC226242
0.8154	Intermediate Similarity	NPC309300
0.8143	Intermediate Similarity	NPC469691
0.8143	Intermediate Similarity	NPC167049
0.8028	Intermediate Similarity	NPC469669
0.8028	Intermediate Similarity	NPC469678
0.8028	Intermediate Similarity	NPC475771
0.8028	Intermediate Similarity	NPC113639
0.8	Intermediate Similarity	NPC165755
0.7969	Intermediate Similarity	NPC252809
0.7857	Intermediate Similarity	NPC471662
0.7778	Intermediate Similarity	NPC7491
0.7778	Intermediate Similarity	NPC101285
0.7778	Intermediate Similarity	NPC27853
0.7778	Intermediate Similarity	NPC13789
0.7778	Intermediate Similarity	NPC65786
0.7761	Intermediate Similarity	NPC19569
0.7746	Intermediate Similarity	NPC329763
0.7727	Intermediate Similarity	NPC474480
0.7727	Intermediate Similarity	NPC283247
0.7639	Intermediate Similarity	NPC27395
0.7639	Intermediate Similarity	NPC471659
0.7639	Intermediate Similarity	NPC329090
0.7576	Intermediate Similarity	NPC210346
0.7564	Intermediate Similarity	NPC474047
0.7538	Intermediate Similarity	NPC83838
0.7538	Intermediate Similarity	NPC143810
0.7536	Intermediate Similarity	NPC136813
0.7536	Intermediate Similarity	NPC472255
0.7536	Intermediate Similarity	NPC472253
0.7534	Intermediate Similarity	NPC328104
0.7534	Intermediate Similarity	NPC319090
0.75	Intermediate Similarity	NPC474140
0.75	Intermediate Similarity	NPC278550
0.75	Intermediate Similarity	NPC476709
0.7468	Intermediate Similarity	NPC474349
0.7468	Intermediate Similarity	NPC474189
0.7467	Intermediate Similarity	NPC474056
0.7467	Intermediate Similarity	NPC474005
0.7463	Intermediate Similarity	NPC279200
0.7436	Intermediate Similarity	NPC475789
0.7436	Intermediate Similarity	NPC108045
0.7436	Intermediate Similarity	NPC475622
0.7432	Intermediate Similarity	NPC310643
0.7432	Intermediate Similarity	NPC315261
0.7432	Intermediate Similarity	NPC476317
0.7429	Intermediate Similarity	NPC224532
0.7429	Intermediate Similarity	NPC167527
0.7429	Intermediate Similarity	NPC160209
0.7424	Intermediate Similarity	NPC135648
0.7424	Intermediate Similarity	NPC127824
0.7403	Intermediate Similarity	NPC472471
0.7403	Intermediate Similarity	NPC471661
0.7391	Intermediate Similarity	NPC272125
0.7391	Intermediate Similarity	NPC469328
0.7391	Intermediate Similarity	NPC327815
0.7375	Intermediate Similarity	NPC125399
0.7375	Intermediate Similarity	NPC137253
0.7368	Intermediate Similarity	NPC44083
0.7368	Intermediate Similarity	NPC153987
0.7361	Intermediate Similarity	NPC471660
0.7353	Intermediate Similarity	NPC225415
0.7342	Intermediate Similarity	NPC475796
0.7333	Intermediate Similarity	NPC318495
0.7333	Intermediate Similarity	NPC34019
0.7333	Intermediate Similarity	NPC471454
0.7333	Intermediate Similarity	NPC155986
0.7333	Intermediate Similarity	NPC198968
0.7333	Intermediate Similarity	NPC476439
0.7324	Intermediate Similarity	NPC239373
0.7324	Intermediate Similarity	NPC329656
0.7324	Intermediate Similarity	NPC269877
0.7324	Intermediate Similarity	NPC304690
0.7324	Intermediate Similarity	NPC74722
0.7324	Intermediate Similarity	NPC167272
0.7324	Intermediate Similarity	NPC329989
0.7313	Intermediate Similarity	NPC274704
0.7297	Intermediate Similarity	NPC28657
0.7297	Intermediate Similarity	NPC136188
0.7297	Intermediate Similarity	NPC22105
0.7297	Intermediate Similarity	NPC162742
0.7297	Intermediate Similarity	NPC230301
0.7297	Intermediate Similarity	NPC285893
0.7297	Intermediate Similarity	NPC141071
0.7297	Intermediate Similarity	NPC257347
0.7297	Intermediate Similarity	NPC288035
0.7297	Intermediate Similarity	NPC471723
0.7297	Intermediate Similarity	NPC304309
0.7297	Intermediate Similarity	NPC134847
0.7286	Intermediate Similarity	NPC259299
0.7286	Intermediate Similarity	NPC477791
0.7273	Intermediate Similarity	NPC472470
0.7237	Intermediate Similarity	NPC302041
0.7237	Intermediate Similarity	NPC285761
0.7237	Intermediate Similarity	NPC85346
0.7237	Intermediate Similarity	NPC65897
0.7222	Intermediate Similarity	NPC475728
0.7222	Intermediate Similarity	NPC470041
0.7222	Intermediate Similarity	NPC9161
0.7222	Intermediate Similarity	NPC49422
0.7215	Intermediate Similarity	NPC139206
0.72	Intermediate Similarity	NPC240604
0.72	Intermediate Similarity	NPC107059
0.72	Intermediate Similarity	NPC471658
0.72	Intermediate Similarity	NPC113733
0.72	Intermediate Similarity	NPC46160
0.72	Intermediate Similarity	NPC129165
0.72	Intermediate Similarity	NPC247325
0.72	Intermediate Similarity	NPC189883
0.72	Intermediate Similarity	NPC202642
0.72	Intermediate Similarity	NPC268111
0.72	Intermediate Similarity	NPC300324
0.72	Intermediate Similarity	NPC237460
0.72	Intermediate Similarity	NPC321381
0.72	Intermediate Similarity	NPC470362
0.72	Intermediate Similarity	NPC244488
0.72	Intermediate Similarity	NPC321016
0.72	Intermediate Similarity	NPC134330
0.7183	Intermediate Similarity	NPC305698
0.7183	Intermediate Similarity	NPC476945
0.7179	Intermediate Similarity	NPC70927
0.716	Intermediate Similarity	NPC261253
0.716	Intermediate Similarity	NPC474045
0.7143	Intermediate Similarity	NPC273410
0.7143	Intermediate Similarity	NPC328714
0.7143	Intermediate Similarity	NPC80530
0.7143	Intermediate Similarity	NPC162309
0.7123	Intermediate Similarity	NPC41886
0.7119	Intermediate Similarity	NPC49088
0.7105	Intermediate Similarity	NPC476703
0.7105	Intermediate Similarity	NPC214570
0.7101	Intermediate Similarity	NPC219940
0.7101	Intermediate Similarity	NPC290367
0.7101	Intermediate Similarity	NPC469723
0.7089	Intermediate Similarity	NPC5985
0.7083	Intermediate Similarity	NPC144647
0.7083	Intermediate Similarity	NPC469677
0.7083	Intermediate Similarity	NPC269841
0.7077	Intermediate Similarity	NPC210316
0.7067	Intermediate Similarity	NPC118508
0.7067	Intermediate Similarity	NPC322353
0.7067	Intermediate Similarity	NPC121744
0.7059	Intermediate Similarity	NPC475251
0.7059	Intermediate Similarity	NPC228574
0.7059	Intermediate Similarity	NPC63111
0.7059	Intermediate Similarity	NPC294304
0.7051	Intermediate Similarity	NPC236237
0.7051	Intermediate Similarity	NPC102253
0.7051	Intermediate Similarity	NPC164840
0.7051	Intermediate Similarity	NPC209944
0.7051	Intermediate Similarity	NPC241290
0.7051	Intermediate Similarity	NPC13554
0.7051	Intermediate Similarity	NPC324772
0.7051	Intermediate Similarity	NPC322313
0.7042	Intermediate Similarity	NPC474477
0.7027	Intermediate Similarity	NPC14352
0.7027	Intermediate Similarity	NPC234527
0.7015	Intermediate Similarity	NPC184049
0.7015	Intermediate Similarity	NPC99480
0.7015	Intermediate Similarity	NPC469321
0.7013	Intermediate Similarity	NPC244385
0.7013	Intermediate Similarity	NPC473943
0.7013	Intermediate Similarity	NPC205455
0.7013	Intermediate Similarity	NPC18603
0.7013	Intermediate Similarity	NPC477514
0.7013	Intermediate Similarity	NPC475337
0.7013	Intermediate Similarity	NPC474216
0.7013	Intermediate Similarity	NPC87604
0.7013	Intermediate Similarity	NPC477522
0.7013	Intermediate Similarity	NPC6978
0.7013	Intermediate Similarity	NPC275910
0.7013	Intermediate Similarity	NPC167037
0.7013	Intermediate Similarity	NPC138621
0.7013	Intermediate Similarity	NPC76931
0.7013	Intermediate Similarity	NPC186191
0.7013	Intermediate Similarity	NPC307965
0.7013	Intermediate Similarity	NPC312328
0.7	Intermediate Similarity	NPC323445
0.7	Intermediate Similarity	NPC61503
0.7	Intermediate Similarity	NPC472473
0.6986	Remote Similarity	NPC475310
0.6974	Remote Similarity	NPC73875
0.6974	Remote Similarity	NPC126969
0.6962	Remote Similarity	NPC474759
0.6962	Remote Similarity	NPC7505
0.6962	Remote Similarity	NPC82986
0.6962	Remote Similarity	NPC474752
0.6962	Remote Similarity	NPC474683
0.6962	Remote Similarity	NPC474731
0.6962	Remote Similarity	NPC47761

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 NPC140233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	3083
0.2-0.3	4186
0.3-0.4	1168
0.4-0.5	272
0.5-0.6	188
0.6-0.7	48
0.7-0.8	0
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
0.7639	Intermediate Similarity	NPD6926	Approved
0.7639	Intermediate Similarity	NPD6924	Approved
0.7432	Intermediate Similarity	NPD6933	Approved
0.7324	Intermediate Similarity	NPD6922	Approved
0.7324	Intermediate Similarity	NPD6923	Approved
0.7297	Intermediate Similarity	NPD7339	Approved
0.7297	Intermediate Similarity	NPD6942	Approved
0.7222	Intermediate Similarity	NPD7143	Approved
0.7222	Intermediate Similarity	NPD7144	Approved
0.7215	Intermediate Similarity	NPD6695	Phase 3
0.7125	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7152	Approved
0.7123	Intermediate Similarity	NPD7151	Approved
0.7123	Intermediate Similarity	NPD7150	Approved
0.7123	Intermediate Similarity	NPD4243	Approved
0.7051	Intermediate Similarity	NPD6930	Phase 2
0.7051	Intermediate Similarity	NPD6931	Approved
0.7051	Intermediate Similarity	NPD7525	Registered
0.6933	Remote Similarity	NPD4784	Approved
0.6933	Remote Similarity	NPD4785	Approved
0.6923	Remote Similarity	NPD6929	Approved
0.6883	Remote Similarity	NPD6932	Approved
0.6867	Remote Similarity	NPD7524	Approved
0.6867	Remote Similarity	NPD7750	Discontinued
0.6835	Remote Similarity	NPD7509	Discontinued
0.6761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6683	Phase 2
0.6706	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD6925	Approved
0.6627	Remote Similarity	NPD6893	Approved
0.6625	Remote Similarity	NPD7514	Phase 3
0.6623	Remote Similarity	NPD5275	Approved
0.6623	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD7145	Approved
0.6582	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7087	Discontinued
0.6548	Remote Similarity	NPD7521	Approved
0.6548	Remote Similarity	NPD7334	Approved
0.6548	Remote Similarity	NPD7146	Approved
0.6548	Remote Similarity	NPD6684	Approved
0.6548	Remote Similarity	NPD5330	Approved
0.6548	Remote Similarity	NPD6409	Approved
0.6543	Remote Similarity	NPD6902	Approved
0.6506	Remote Similarity	NPD4786	Approved
0.642	Remote Similarity	NPD7332	Phase 2
0.6395	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6903	Approved
0.6395	Remote Similarity	NPD5737	Approved
0.6395	Remote Similarity	NPD6672	Approved
0.6375	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6098	Approved
0.6341	Remote Similarity	NPD6898	Phase 1
0.6296	Remote Similarity	NPD7645	Phase 2
0.6296	Remote Similarity	NPD4195	Approved
0.6292	Remote Similarity	NPD6399	Phase 3
0.6279	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4748	Discontinued
0.6197	Remote Similarity	NPD1145	Discontinued
0.619	Remote Similarity	NPD5362	Discontinued
0.6163	Remote Similarity	NPD5279	Phase 3
0.6154	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5369	Approved
0.6136	Remote Similarity	NPD5328	Approved
0.6136	Remote Similarity	NPD6904	Approved
0.6136	Remote Similarity	NPD6080	Approved
0.6136	Remote Similarity	NPD6673	Approved
0.6136	Remote Similarity	NPD1695	Approved
0.6118	Remote Similarity	NPD3666	Approved
0.6118	Remote Similarity	NPD3133	Approved
0.6118	Remote Similarity	NPD3668	Phase 3
0.6118	Remote Similarity	NPD3665	Phase 1
0.6111	Remote Similarity	NPD368	Approved
0.6071	Remote Similarity	NPD4223	Phase 3
0.6071	Remote Similarity	NPD4221	Approved
0.6071	Remote Similarity	NPD6435	Approved
0.6047	Remote Similarity	NPD5329	Approved
0.6024	Remote Similarity	NPD4819	Approved
0.6024	Remote Similarity	NPD4822	Approved
0.6024	Remote Similarity	NPD4821	Approved
0.6024	Remote Similarity	NPD4820	Approved
0.6024	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5208	Approved
0.6022	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD8264	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD5332	Approved
0.5978	Remote Similarity	NPD5695	Phase 3
0.5977	Remote Similarity	NPD3618	Phase 1
0.5955	Remote Similarity	NPD4753	Phase 2
0.5952	Remote Similarity	NPD4790	Discontinued
0.5942	Remote Similarity	NPD342	Phase 1
0.5934	Remote Similarity	NPD4202	Approved
0.593	Remote Similarity	NPD4197	Approved
0.5918	Remote Similarity	NPD6008	Approved
0.5889	Remote Similarity	NPD5692	Phase 3
0.5889	Remote Similarity	NPD5207	Approved
0.5882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5209	Approved
0.587	Remote Similarity	NPD6001	Approved
0.5833	Remote Similarity	NPD5368	Approved
0.5824	Remote Similarity	NPD5693	Phase 1
0.5824	Remote Similarity	NPD5694	Approved
0.5814	Remote Similarity	NPD7154	Phase 3
0.5814	Remote Similarity	NPD4788	Approved
0.5802	Remote Similarity	NPD8039	Approved
0.5795	Remote Similarity	NPD5690	Phase 2
0.5795	Remote Similarity	NPD5205	Approved
0.5795	Remote Similarity	NPD4138	Approved
0.5795	Remote Similarity	NPD4690	Approved
0.5795	Remote Similarity	NPD4694	Approved
0.5795	Remote Similarity	NPD4693	Phase 3
0.5795	Remote Similarity	NPD4688	Approved
0.5795	Remote Similarity	NPD4689	Approved
0.5795	Remote Similarity	NPD5280	Approved
0.5789	Remote Similarity	NPD7638	Approved
0.5789	Remote Similarity	NPD5696	Approved
0.5783	Remote Similarity	NPD4271	Approved
0.5783	Remote Similarity	NPD4268	Approved
0.5758	Remote Similarity	NPD5739	Approved
0.5758	Remote Similarity	NPD6402	Approved
0.5758	Remote Similarity	NPD7128	Approved
0.5758	Remote Similarity	NPD6675	Approved
0.5733	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7639	Approved
0.5729	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD5785	Approved
0.5714	Remote Similarity	NPD3168	Discontinued
0.5699	Remote Similarity	NPD5282	Discontinued
0.5699	Remote Similarity	NPD5707	Approved
0.5698	Remote Similarity	NPD4270	Approved
0.5698	Remote Similarity	NPD4269	Approved
0.5696	Remote Similarity	NPD4747	Approved
0.5684	Remote Similarity	NPD4755	Approved
0.5682	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD1694	Approved
0.5679	Remote Similarity	NPD5733	Approved
0.5667	Remote Similarity	NPD4518	Approved
0.5667	Remote Similarity	NPD4723	Approved
0.5667	Remote Similarity	NPD4722	Approved
0.5652	Remote Similarity	NPD8034	Phase 2
0.5652	Remote Similarity	NPD6411	Approved
0.5652	Remote Similarity	NPD8035	Phase 2
0.5644	Remote Similarity	NPD6899	Approved
0.5644	Remote Similarity	NPD6881	Approved
0.5644	Remote Similarity	NPD7320	Approved
0.5641	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4629	Approved
0.5638	Remote Similarity	NPD5210	Approved
0.5634	Remote Similarity	NPD4219	Approved
0.5625	Remote Similarity	NPD5276	Approved
0.5618	Remote Similarity	NPD5786	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