NPASS Compound

Structure

CID92909 OpenBabel06191715432D 22 24 0 0 1 0 0 0 0 0999 V2000 2.1533 -3.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5933 -4.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5259 2.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0677 -0.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7233 -2.1690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1911 1.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3256 1.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 0.9952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2554 -1.6438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1691 0.0794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3747 -1.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5480 -2.2657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1133 -3.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1438 1.6099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5933 -2.3661 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2028 -1.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7476 -1.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8221 0.4957 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9162 -0.8467 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8404 -0.4641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6246 -0.9362 0.0000 O 0 0 0 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 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 15 13 1 6 0 0 0 15 16 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 1 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.391
LogD:	3.771
LogS:	-4.317
# Rotatable Bonds:	1
TPSA:	29.6
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.863
Fsp3:	0.75
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:	-4.587
MDCK Permeability:	1.882630203908775e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	79.4646224975586%
Volume Distribution (VD):	1.662
Pgp-substrate:	15.881832122802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.407
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	14.802
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.844
Carcinogencity:	0.899
Eye Corrosion:	0.89
Eye Irritation:	0.758
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: NPC92909

Natural Product ID:	NPC92909
*Common Name:**	BGCBFCPMURPDPJ-WIFYINSBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BGCBFCPMURPDPJ-WIFYINSBSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)15-12-17(21)19(4)10-8-14(3)6-7-18-20(5,22-18)11-9-16(15)19/h8,15-16,18H,1,6-7,9-12H2,2-5H3/b14-8-/t15-,16+,18+,19-,20+/m1/s1
SMILES:	C=C(C)[C@H]1CC(=O)[C@]2(C)C/C=C(/C)CC[C@H]3[C@](C)(CC[C@@H]12)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689081
PubChem CID:	51040056
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.	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]
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]
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[460937]

☑ 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 NPC92909 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	193
0.1-0.2	1637
0.2-0.3	9867
0.3-0.4	14442
0.4-0.5	7011
0.5-0.6	6708
0.6-0.7	2562
0.7-0.8	256
0.8-0.85	7
0.85-0.9	9
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC107783
0.9571	High Similarity	NPC226242
0.9565	High Similarity	NPC167049
0.9565	High Similarity	NPC469691
0.9429	High Similarity	NPC469669
0.9429	High Similarity	NPC469678
0.9429	High Similarity	NPC475771
0.8784	High Similarity	NPC474056
0.859	High Similarity	NPC475796
0.8529	High Similarity	NPC287744
0.8529	High Similarity	NPC140233
0.8462	Intermediate Similarity	NPC475622
0.8462	Intermediate Similarity	NPC108045
0.8194	Intermediate Similarity	NPC477449
0.8194	Intermediate Similarity	NPC469677
0.8194	Intermediate Similarity	NPC477448
0.8182	Intermediate Similarity	NPC469608
0.8148	Intermediate Similarity	NPC474045
0.8148	Intermediate Similarity	NPC261253
0.7949	Intermediate Similarity	NPC469690
0.7945	Intermediate Similarity	NPC22301
0.7927	Intermediate Similarity	NPC469676
0.7922	Intermediate Similarity	NPC186109
0.791	Intermediate Similarity	NPC267626
0.791	Intermediate Similarity	NPC55004
0.791	Intermediate Similarity	NPC49575
0.7895	Intermediate Similarity	NPC475861
0.7882	Intermediate Similarity	NPC262870
0.7875	Intermediate Similarity	NPC145963
0.7867	Intermediate Similarity	NPC470237
0.7838	Intermediate Similarity	NPC475310
0.7821	Intermediate Similarity	NPC207186
0.7808	Intermediate Similarity	NPC469688
0.7792	Intermediate Similarity	NPC215481
0.7792	Intermediate Similarity	NPC271070
0.7792	Intermediate Similarity	NPC469646
0.7778	Intermediate Similarity	NPC470047
0.7778	Intermediate Similarity	NPC470046
0.7722	Intermediate Similarity	NPC469620
0.7722	Intermediate Similarity	NPC476177
0.7711	Intermediate Similarity	NPC470050
0.7711	Intermediate Similarity	NPC470051
0.7703	Intermediate Similarity	NPC144511
0.7703	Intermediate Similarity	NPC261398
0.7703	Intermediate Similarity	NPC296522
0.7701	Intermediate Similarity	NPC67831
0.7701	Intermediate Similarity	NPC174051
0.7692	Intermediate Similarity	NPC276769
0.7683	Intermediate Similarity	NPC100391
0.7681	Intermediate Similarity	NPC259261
0.7662	Intermediate Similarity	NPC474419
0.7662	Intermediate Similarity	NPC113639
0.7662	Intermediate Similarity	NPC251435
0.7647	Intermediate Similarity	NPC230823
0.759	Intermediate Similarity	NPC202868
0.759	Intermediate Similarity	NPC323765
0.759	Intermediate Similarity	NPC96621
0.759	Intermediate Similarity	NPC470048
0.759	Intermediate Similarity	NPC470223
0.7571	Intermediate Similarity	NPC25853
0.7568	Intermediate Similarity	NPC469679
0.7561	Intermediate Similarity	NPC476082
0.7561	Intermediate Similarity	NPC278648
0.7558	Intermediate Similarity	NPC306168
0.7558	Intermediate Similarity	NPC49946
0.7536	Intermediate Similarity	NPC266295
0.7536	Intermediate Similarity	NPC94991
0.7536	Intermediate Similarity	NPC30215
0.7532	Intermediate Similarity	NPC206875
0.7531	Intermediate Similarity	NPC136150
0.7529	Intermediate Similarity	NPC28227
0.7528	Intermediate Similarity	NPC477354
0.75	Intermediate Similarity	NPC261125
0.75	Intermediate Similarity	NPC617
0.75	Intermediate Similarity	NPC195640
0.75	Intermediate Similarity	NPC181195
0.75	Intermediate Similarity	NPC215843
0.75	Intermediate Similarity	NPC264127
0.75	Intermediate Similarity	NPC80999
0.75	Intermediate Similarity	NPC229204
0.75	Intermediate Similarity	NPC473902
0.747	Intermediate Similarity	NPC221758
0.747	Intermediate Similarity	NPC59453
0.747	Intermediate Similarity	NPC473246
0.747	Intermediate Similarity	NPC82902
0.747	Intermediate Similarity	NPC85774
0.747	Intermediate Similarity	NPC214043
0.7468	Intermediate Similarity	NPC195785
0.7468	Intermediate Similarity	NPC15975
0.7468	Intermediate Similarity	NPC476325
0.7468	Intermediate Similarity	NPC476264
0.7465	Intermediate Similarity	NPC228574
0.7465	Intermediate Similarity	NPC294304
0.7465	Intermediate Similarity	NPC475795
0.7444	Intermediate Similarity	NPC151488
0.7442	Intermediate Similarity	NPC170775
0.7439	Intermediate Similarity	NPC328351
0.7439	Intermediate Similarity	NPC240302
0.7439	Intermediate Similarity	NPC151519
0.7436	Intermediate Similarity	NPC474011
0.7436	Intermediate Similarity	NPC77501
0.7412	Intermediate Similarity	NPC167877
0.7412	Intermediate Similarity	NPC90652
0.7407	Intermediate Similarity	NPC47747
0.7407	Intermediate Similarity	NPC304795
0.7386	Intermediate Similarity	NPC477361
0.7386	Intermediate Similarity	NPC202824
0.7386	Intermediate Similarity	NPC37816
0.7381	Intermediate Similarity	NPC474083
0.7381	Intermediate Similarity	NPC471224
0.7381	Intermediate Similarity	NPC474218
0.7375	Intermediate Similarity	NPC474341
0.7375	Intermediate Similarity	NPC35574
0.7375	Intermediate Similarity	NPC469996
0.7368	Intermediate Similarity	NPC472955
0.7363	Intermediate Similarity	NPC477355
0.7353	Intermediate Similarity	NPC223604
0.7349	Intermediate Similarity	NPC193198
0.7349	Intermediate Similarity	NPC473629
0.7349	Intermediate Similarity	NPC475989
0.7342	Intermediate Similarity	NPC471726
0.7342	Intermediate Similarity	NPC476317
0.7342	Intermediate Similarity	NPC474527
0.7326	Intermediate Similarity	NPC97884
0.7326	Intermediate Similarity	NPC470417
0.7326	Intermediate Similarity	NPC472220
0.7326	Intermediate Similarity	NPC193360
0.7317	Intermediate Similarity	NPC207188
0.7317	Intermediate Similarity	NPC39411
0.7317	Intermediate Similarity	NPC475665
0.7317	Intermediate Similarity	NPC255580
0.7317	Intermediate Similarity	NPC141810
0.7308	Intermediate Similarity	NPC469643
0.7308	Intermediate Similarity	NPC469641
0.7308	Intermediate Similarity	NPC472966
0.7297	Intermediate Similarity	NPC304665
0.7297	Intermediate Similarity	NPC126899
0.7297	Intermediate Similarity	NPC154728
0.7294	Intermediate Similarity	NPC474733
0.7294	Intermediate Similarity	NPC469994
0.7294	Intermediate Similarity	NPC473168
0.7294	Intermediate Similarity	NPC145879
0.7294	Intermediate Similarity	NPC31564
0.7294	Intermediate Similarity	NPC474732
0.7294	Intermediate Similarity	NPC474778
0.7294	Intermediate Similarity	NPC89077
0.7294	Intermediate Similarity	NPC51014
0.7284	Intermediate Similarity	NPC182550
0.7284	Intermediate Similarity	NPC477371
0.7284	Intermediate Similarity	NPC7232
0.7283	Intermediate Similarity	NPC112167
0.7273	Intermediate Similarity	NPC221282
0.7273	Intermediate Similarity	NPC190442
0.7273	Intermediate Similarity	NPC218301
0.7273	Intermediate Similarity	NPC40327
0.7262	Intermediate Similarity	NPC329043
0.7262	Intermediate Similarity	NPC227064
0.7262	Intermediate Similarity	NPC238197
0.7262	Intermediate Similarity	NPC58841
0.7262	Intermediate Similarity	NPC165064
0.7262	Intermediate Similarity	NPC237712
0.7262	Intermediate Similarity	NPC161423
0.7262	Intermediate Similarity	NPC321187
0.7262	Intermediate Similarity	NPC109512
0.7262	Intermediate Similarity	NPC90446
0.7262	Intermediate Similarity	NPC475100
0.7262	Intermediate Similarity	NPC25833
0.725	Intermediate Similarity	NPC122264
0.7241	Intermediate Similarity	NPC2983
0.7241	Intermediate Similarity	NPC32830
0.7241	Intermediate Similarity	NPC76879
0.7241	Intermediate Similarity	NPC474679
0.7241	Intermediate Similarity	NPC474245
0.7241	Intermediate Similarity	NPC474570
0.7237	Intermediate Similarity	NPC199557
0.7237	Intermediate Similarity	NPC61702
0.7237	Intermediate Similarity	NPC5714
0.7237	Intermediate Similarity	NPC162867
0.7229	Intermediate Similarity	NPC256750
0.7229	Intermediate Similarity	NPC193347
0.7229	Intermediate Similarity	NPC475936
0.7229	Intermediate Similarity	NPC20262
0.7222	Intermediate Similarity	NPC472469
0.7215	Intermediate Similarity	NPC324762
0.7215	Intermediate Similarity	NPC114236
0.7215	Intermediate Similarity	NPC216791
0.7209	Intermediate Similarity	NPC475740
0.7209	Intermediate Similarity	NPC317590
0.7209	Intermediate Similarity	NPC136548
0.7209	Intermediate Similarity	NPC469322
0.7209	Intermediate Similarity	NPC58063
0.7204	Intermediate Similarity	NPC476897
0.7204	Intermediate Similarity	NPC477356
0.72	Intermediate Similarity	NPC469868
0.7195	Intermediate Similarity	NPC170038
0.7195	Intermediate Similarity	NPC276356
0.7195	Intermediate Similarity	NPC472478
0.7195	Intermediate Similarity	NPC45495
0.7191	Intermediate Similarity	NPC229976
0.7191	Intermediate Similarity	NPC125180

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 NPC92909 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2336
0.2-0.3	4300
0.3-0.4	1556
0.4-0.5	397
0.5-0.6	241
0.6-0.7	134
0.7-0.8	8
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
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.747	Intermediate Similarity	NPD4786	Approved
0.7439	Intermediate Similarity	NPD3667	Approved
0.7375	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6903	Approved
0.7326	Intermediate Similarity	NPD6672	Approved
0.7326	Intermediate Similarity	NPD5737	Approved
0.7326	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5279	Phase 3
0.7294	Intermediate Similarity	NPD6098	Approved
0.7262	Intermediate Similarity	NPD3133	Approved
0.7262	Intermediate Similarity	NPD3665	Phase 1
0.7262	Intermediate Similarity	NPD3668	Phase 3
0.7262	Intermediate Similarity	NPD3666	Approved
0.7229	Intermediate Similarity	NPD4221	Approved
0.7229	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD6399	Phase 3
0.7126	Intermediate Similarity	NPD5208	Approved
0.7108	Intermediate Similarity	NPD5369	Approved
0.7093	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD4197	Approved
0.7045	Intermediate Similarity	NPD6904	Approved
0.7045	Intermediate Similarity	NPD6080	Approved
0.7045	Intermediate Similarity	NPD1695	Approved
0.7045	Intermediate Similarity	NPD4753	Phase 2
0.7045	Intermediate Similarity	NPD5328	Approved
0.7045	Intermediate Similarity	NPD6673	Approved
0.7033	Intermediate Similarity	NPD5695	Phase 3
0.7033	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6435	Approved
0.7	Intermediate Similarity	NPD4202	Approved
0.6977	Remote Similarity	NPD5329	Approved
0.6966	Remote Similarity	NPD5692	Phase 3
0.6966	Remote Similarity	NPD5207	Approved
0.6941	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD4747	Approved
0.6907	Remote Similarity	NPD6008	Approved
0.6897	Remote Similarity	NPD4690	Approved
0.6897	Remote Similarity	NPD5690	Phase 2
0.6897	Remote Similarity	NPD4689	Approved
0.6897	Remote Similarity	NPD4693	Phase 3
0.6897	Remote Similarity	NPD4688	Approved
0.6897	Remote Similarity	NPD5280	Approved
0.6897	Remote Similarity	NPD5205	Approved
0.6897	Remote Similarity	NPD4138	Approved
0.6897	Remote Similarity	NPD4694	Approved
0.6889	Remote Similarity	NPD6079	Approved
0.6889	Remote Similarity	NPD5694	Approved
0.6889	Remote Similarity	NPD6050	Approved
0.6889	Remote Similarity	NPD5693	Phase 1
0.6882	Remote Similarity	NPD6084	Phase 2
0.6882	Remote Similarity	NPD6083	Phase 2
0.6875	Remote Similarity	NPD6924	Approved
0.6875	Remote Similarity	NPD6926	Approved
0.6835	Remote Similarity	NPD5276	Approved
0.6824	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5696	Approved
0.6795	Remote Similarity	NPD4137	Phase 3
0.6786	Remote Similarity	NPD5368	Approved
0.6782	Remote Similarity	NPD1694	Approved
0.6744	Remote Similarity	NPD4788	Approved
0.6742	Remote Similarity	NPD4518	Approved
0.6739	Remote Similarity	NPD5282	Discontinued
0.6711	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4691	Approved
0.6707	Remote Similarity	NPD6933	Approved
0.6706	Remote Similarity	NPD4139	Approved
0.6706	Remote Similarity	NPD4692	Approved
0.6702	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4270	Approved
0.6628	Remote Similarity	NPD4269	Approved
0.6628	Remote Similarity	NPD5209	Approved
0.6623	Remote Similarity	NPD7331	Phase 2
0.6596	Remote Similarity	NPD5221	Approved
0.6596	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5222	Approved
0.6593	Remote Similarity	NPD4096	Approved
0.6593	Remote Similarity	NPD5785	Approved
0.6591	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8039	Approved
0.6566	Remote Similarity	NPD5739	Approved
0.6566	Remote Similarity	NPD7128	Approved
0.6566	Remote Similarity	NPD6675	Approved
0.6566	Remote Similarity	NPD6402	Approved
0.6562	Remote Similarity	NPD5286	Approved
0.6562	Remote Similarity	NPD5285	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.6562	Remote Similarity	NPD4696	Approved
0.6552	Remote Similarity	NPD6695	Phase 3
0.6552	Remote Similarity	NPD7154	Phase 3
0.6548	Remote Similarity	NPD3617	Approved
0.6526	Remote Similarity	NPD5173	Approved
0.6526	Remote Similarity	NPD5959	Approved
0.6522	Remote Similarity	NPD5281	Approved
0.6522	Remote Similarity	NPD5284	Approved
0.6517	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5786	Approved
0.65	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD5697	Approved
0.6495	Remote Similarity	NPD5223	Approved
0.6494	Remote Similarity	NPD7341	Phase 2
0.6489	Remote Similarity	NPD5654	Approved
0.6484	Remote Similarity	NPD6051	Approved
0.6477	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4195	Approved
0.6463	Remote Similarity	NPD4058	Approved
0.6452	Remote Similarity	NPD5133	Approved
0.6444	Remote Similarity	NPD3573	Approved
0.6436	Remote Similarity	NPD6881	Approved
0.6436	Remote Similarity	NPD6899	Approved
0.6436	Remote Similarity	NPD6011	Approved
0.6436	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD5363	Approved
0.6404	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD6931	Approved
0.6395	Remote Similarity	NPD4695	Discontinued
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD7525	Registered
0.6395	Remote Similarity	NPD6930	Phase 2
0.6395	Remote Similarity	NPD4252	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6386	Remote Similarity	NPD6942	Approved
0.6386	Remote Similarity	NPD7339	Approved
0.6383	Remote Similarity	NPD7748	Approved
0.6383	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7900	Approved
0.6375	Remote Similarity	NPD6923	Approved
0.6375	Remote Similarity	NPD6922	Approved
0.6373	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD6012	Approved
0.6373	Remote Similarity	NPD6373	Approved
0.6373	Remote Similarity	NPD6013	Approved
0.6373	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD5331	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD5332	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6344	Remote Similarity	NPD8035	Phase 2
0.6344	Remote Similarity	NPD6411	Approved
0.6344	Remote Similarity	NPD8034	Phase 2
0.6333	Remote Similarity	NPD4519	Discontinued
0.6333	Remote Similarity	NPD4623	Approved
0.6322	Remote Similarity	NPD4790	Discontinued
0.6316	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD7290	Approved
0.6311	Remote Similarity	NPD6883	Approved
0.631	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5141	Approved
0.6296	Remote Similarity	NPD7144	Approved
0.6296	Remote Similarity	NPD7143	Approved
0.6282	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6929	Approved
0.6264	Remote Similarity	NPD7524	Approved
0.6264	Remote Similarity	NPD7750	Discontinued
0.6262	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.6238	Remote Similarity	NPD4767	Approved
0.6238	Remote Similarity	NPD4768	Approved
0.6235	Remote Similarity	NPD6932	Approved
0.622	Remote Similarity	NPD4243	Approved
0.622	Remote Similarity	NPD7151	Approved
0.622	Remote Similarity	NPD7150	Approved
0.622	Remote Similarity	NPD7152	Approved
0.622	Remote Similarity	NPD5777	Approved
0.6207	Remote Similarity	NPD7509	Discontinued
0.62	Remote Similarity	NPD6052	Approved
0.619	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD6882	Approved
0.6186	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD6412	Phase 2
0.617	Remote Similarity	NPD7637	Suspended

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