NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	2.772
LogD:	1.748
LogS:	-3.469
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	4.227
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.542
MDCK Permeability:	2.547921940276865e-05
Pgp-inhibitor:	0.126
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.289

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.774
Plasma Protein Binding (PPB):	86.25220489501953%
Volume Distribution (VD):	1.221
Pgp-substrate:	12.587067604064941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.768
CYP2C19-inhibitor:	0.331
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.266
CYP2D6-inhibitor:	0.093
CYP2D6-substrate:	0.405
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	4.823
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.766
Carcinogencity:	0.162
Eye Corrosion:	0.204
Eye Irritation:	0.781
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC77501

Natural Product ID:	NPC77501
*Common Name:**	(1R,4R)-4-Hydroxydauca-7-Ene-6-One
IUPAC Name:	(3R,3aR,8aS)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-2,3a,7,8-tetrahydro-1H-azulen-4-one
Synonyms:
Standard InCHIKey:	QUTYSAHKWGWCNV-QLFBSQMISA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-10(2)15(17)8-7-14(4)6-5-11(3)9-12(16)13(14)15/h9-10,13,17H,5-8H2,1-4H3/t13-,14+,15-/m1/s1
SMILES:	CC1=CC(=O)[C@@H]2[C@](CC1)(C)CC[C@@]2(O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469710
PubChem CID:	11447717
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277769]
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787464]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	308.2	%	PMID[528743]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	97.5	%	PMID[528743]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	181.4	%	PMID[528743]

☑ 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 NPC77501 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	172
0.1-0.2	1613
0.2-0.3	10054
0.3-0.4	15248
0.4-0.5	7805
0.5-0.6	5813
0.6-0.7	1714
0.7-0.8	250
0.8-0.85	21
0.85-0.9	2
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC164218
0.9155	High Similarity	NPC300940
0.8904	High Similarity	NPC251435
0.875	High Similarity	NPC469737
0.8533	High Similarity	NPC215481
0.8442	Intermediate Similarity	NPC471890
0.8442	Intermediate Similarity	NPC84185
0.8442	Intermediate Similarity	NPC66677
0.8354	Intermediate Similarity	NPC20262
0.8354	Intermediate Similarity	NPC256750
0.8333	Intermediate Similarity	NPC30675
0.8289	Intermediate Similarity	NPC25908
0.8289	Intermediate Similarity	NPC115719
0.8289	Intermediate Similarity	NPC142759
0.8289	Intermediate Similarity	NPC141346
0.8289	Intermediate Similarity	NPC473437
0.8289	Intermediate Similarity	NPC124289
0.8267	Intermediate Similarity	NPC7382
0.8158	Intermediate Similarity	NPC89374
0.8148	Intermediate Similarity	NPC90446
0.8125	Intermediate Similarity	NPC133844
0.8125	Intermediate Similarity	NPC193347
0.8095	Intermediate Similarity	NPC170775
0.8052	Intermediate Similarity	NPC182848
0.7975	Intermediate Similarity	NPC181195
0.7975	Intermediate Similarity	NPC301769
0.7975	Intermediate Similarity	NPC261125
0.7975	Intermediate Similarity	NPC32758
0.7949	Intermediate Similarity	NPC276769
0.7927	Intermediate Similarity	NPC144258
0.7922	Intermediate Similarity	NPC201263
0.7882	Intermediate Similarity	NPC41217
0.7875	Intermediate Similarity	NPC45495
0.7848	Intermediate Similarity	NPC476627
0.7821	Intermediate Similarity	NPC469646
0.7805	Intermediate Similarity	NPC62214
0.7792	Intermediate Similarity	NPC206875
0.7791	Intermediate Similarity	NPC2946
0.7765	Intermediate Similarity	NPC58532
0.7765	Intermediate Similarity	NPC472677
0.775	Intermediate Similarity	NPC7232
0.775	Intermediate Similarity	NPC472013
0.775	Intermediate Similarity	NPC476624
0.7714	Intermediate Similarity	NPC259261
0.7714	Intermediate Similarity	NPC469321
0.7711	Intermediate Similarity	NPC472480
0.7683	Intermediate Similarity	NPC129080
0.7683	Intermediate Similarity	NPC477269
0.7683	Intermediate Similarity	NPC477270
0.7683	Intermediate Similarity	NPC477271
0.7654	Intermediate Similarity	NPC233352
0.7654	Intermediate Similarity	NPC824
0.7654	Intermediate Similarity	NPC138492
0.7619	Intermediate Similarity	NPC476628
0.7619	Intermediate Similarity	NPC142649
0.7606	Intermediate Similarity	NPC252809
0.7606	Intermediate Similarity	NPC25853
0.759	Intermediate Similarity	NPC474748
0.759	Intermediate Similarity	NPC477373
0.7571	Intermediate Similarity	NPC266295
0.7571	Intermediate Similarity	NPC94991
0.7568	Intermediate Similarity	NPC197089
0.7564	Intermediate Similarity	NPC469691
0.7564	Intermediate Similarity	NPC167049
0.7561	Intermediate Similarity	NPC477372
0.7561	Intermediate Similarity	NPC136150
0.7558	Intermediate Similarity	NPC320665
0.7534	Intermediate Similarity	NPC473902
0.7532	Intermediate Similarity	NPC144627
0.7532	Intermediate Similarity	NPC29328
0.7532	Intermediate Similarity	NPC106309
0.7531	Intermediate Similarity	NPC229204
0.7531	Intermediate Similarity	NPC215843
0.7529	Intermediate Similarity	NPC6247
0.7528	Intermediate Similarity	NPC298919
0.75	Intermediate Similarity	NPC161423
0.75	Intermediate Similarity	NPC321187
0.75	Intermediate Similarity	NPC227064
0.75	Intermediate Similarity	NPC329043
0.75	Intermediate Similarity	NPC61702
0.75	Intermediate Similarity	NPC162867
0.75	Intermediate Similarity	NPC58841
0.7473	Intermediate Similarity	NPC477949
0.7471	Intermediate Similarity	NPC310010
0.7471	Intermediate Similarity	NPC326627
0.747	Intermediate Similarity	NPC320514
0.7468	Intermediate Similarity	NPC474011
0.7468	Intermediate Similarity	NPC475771
0.7468	Intermediate Similarity	NPC469678
0.7468	Intermediate Similarity	NPC469669
0.7467	Intermediate Similarity	NPC476626
0.7465	Intermediate Similarity	NPC143834
0.7442	Intermediate Similarity	NPC472482
0.7442	Intermediate Similarity	NPC472484
0.7442	Intermediate Similarity	NPC472481
0.7439	Intermediate Similarity	NPC279667
0.7439	Intermediate Similarity	NPC471656
0.7436	Intermediate Similarity	NPC92909
0.7436	Intermediate Similarity	NPC107783
0.7432	Intermediate Similarity	NPC205618
0.7432	Intermediate Similarity	NPC261782
0.7432	Intermediate Similarity	NPC469326
0.7432	Intermediate Similarity	NPC474329
0.7432	Intermediate Similarity	NPC474304
0.7429	Intermediate Similarity	NPC267626
0.7429	Intermediate Similarity	NPC55004
0.7429	Intermediate Similarity	NPC49575
0.7429	Intermediate Similarity	NPC278550
0.7412	Intermediate Similarity	NPC179006
0.7412	Intermediate Similarity	NPC474853
0.7412	Intermediate Similarity	NPC36350
0.7412	Intermediate Similarity	NPC245434
0.7407	Intermediate Similarity	NPC19443
0.7403	Intermediate Similarity	NPC280256
0.7403	Intermediate Similarity	NPC18543
0.7397	Intermediate Similarity	NPC474480
0.7397	Intermediate Similarity	NPC165695
0.7381	Intermediate Similarity	NPC65350
0.7381	Intermediate Similarity	NPC472492
0.7381	Intermediate Similarity	NPC470165
0.7368	Intermediate Similarity	NPC469688
0.7368	Intermediate Similarity	NPC476614
0.7363	Intermediate Similarity	NPC9812
0.7356	Intermediate Similarity	NPC328313
0.7356	Intermediate Similarity	NPC472483
0.7356	Intermediate Similarity	NPC477710
0.7349	Intermediate Similarity	NPC171665
0.7326	Intermediate Similarity	NPC472479
0.7326	Intermediate Similarity	NPC476043
0.7324	Intermediate Similarity	NPC30215
0.7317	Intermediate Similarity	NPC164308
0.7317	Intermediate Similarity	NPC477371
0.7308	Intermediate Similarity	NPC41886
0.7308	Intermediate Similarity	NPC288667
0.7297	Intermediate Similarity	NPC212210
0.7294	Intermediate Similarity	NPC7927
0.7294	Intermediate Similarity	NPC475796
0.7294	Intermediate Similarity	NPC473246
0.7294	Intermediate Similarity	NPC85774
0.7294	Intermediate Similarity	NPC82902
0.7294	Intermediate Similarity	NPC237712
0.7294	Intermediate Similarity	NPC214043
0.7294	Intermediate Similarity	NPC230527
0.7284	Intermediate Similarity	NPC257666
0.7284	Intermediate Similarity	NPC472014
0.7284	Intermediate Similarity	NPC86917
0.7284	Intermediate Similarity	NPC266193
0.7283	Intermediate Similarity	NPC477267
0.7283	Intermediate Similarity	NPC477268
0.7283	Intermediate Similarity	NPC472690
0.7283	Intermediate Similarity	NPC472689
0.7273	Intermediate Similarity	NPC469914
0.7273	Intermediate Similarity	NPC477943
0.7273	Intermediate Similarity	NPC469677
0.726	Intermediate Similarity	NPC63111
0.726	Intermediate Similarity	NPC475795
0.726	Intermediate Similarity	NPC213152
0.725	Intermediate Similarity	NPC114236
0.7241	Intermediate Similarity	NPC136948
0.7237	Intermediate Similarity	NPC60120
0.7237	Intermediate Similarity	NPC136813
0.7234	Intermediate Similarity	NPC206079
0.7234	Intermediate Similarity	NPC477950
0.7229	Intermediate Similarity	NPC47747
0.7229	Intermediate Similarity	NPC472478
0.7222	Intermediate Similarity	NPC37816
0.7222	Intermediate Similarity	NPC5698
0.7222	Intermediate Similarity	NPC474807
0.7222	Intermediate Similarity	NPC233118
0.7222	Intermediate Similarity	NPC125180
0.7215	Intermediate Similarity	NPC275098
0.7209	Intermediate Similarity	NPC132629
0.7209	Intermediate Similarity	NPC474218
0.7209	Intermediate Similarity	NPC29447
0.7209	Intermediate Similarity	NPC15838
0.7209	Intermediate Similarity	NPC469948
0.7204	Intermediate Similarity	NPC64742
0.7204	Intermediate Similarity	NPC244411
0.7195	Intermediate Similarity	NPC471409
0.7195	Intermediate Similarity	NPC275494
0.7195	Intermediate Similarity	NPC207772
0.7191	Intermediate Similarity	NPC477711
0.7183	Intermediate Similarity	NPC193695
0.7183	Intermediate Similarity	NPC230823
0.7176	Intermediate Similarity	NPC168188
0.7176	Intermediate Similarity	NPC470015
0.7176	Intermediate Similarity	NPC477852
0.7162	Intermediate Similarity	NPC32285
0.716	Intermediate Similarity	NPC263582
0.716	Intermediate Similarity	NPC180886
0.716	Intermediate Similarity	NPC226242
0.716	Intermediate Similarity	NPC470525
0.7159	Intermediate Similarity	NPC471941
0.7159	Intermediate Similarity	NPC474854
0.7143	Intermediate Similarity	NPC472684
0.7143	Intermediate Similarity	NPC124207
0.7143	Intermediate Similarity	NPC150506
0.7143	Intermediate Similarity	NPC189237
0.7143	Intermediate Similarity	NPC38350
0.7143	Intermediate Similarity	NPC47031

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 NPC77501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	2338
0.2-0.3	4296
0.3-0.4	1623
0.4-0.5	358
0.5-0.6	222
0.6-0.7	112
0.7-0.8	30
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
0.8125	Intermediate Similarity	NPD4223	Phase 3
0.8125	Intermediate Similarity	NPD4221	Approved
0.7927	Intermediate Similarity	NPD4197	Approved
0.7831	Intermediate Similarity	NPD5329	Approved
0.7738	Intermediate Similarity	NPD4689	Approved
0.7738	Intermediate Similarity	NPD4693	Phase 3
0.7738	Intermediate Similarity	NPD4694	Approved
0.7738	Intermediate Similarity	NPD5690	Phase 2
0.7738	Intermediate Similarity	NPD4138	Approved
0.7738	Intermediate Similarity	NPD4688	Approved
0.7738	Intermediate Similarity	NPD4690	Approved
0.7738	Intermediate Similarity	NPD5280	Approved
0.7738	Intermediate Similarity	NPD5205	Approved
0.7558	Intermediate Similarity	NPD4518	Approved
0.7529	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.7471	Intermediate Similarity	NPD4753	Phase 2
0.7386	Intermediate Similarity	NPD4096	Approved
0.7349	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD7331	Phase 2
0.7317	Intermediate Similarity	NPD4195	Approved
0.7303	Intermediate Similarity	NPD5284	Approved
0.7303	Intermediate Similarity	NPD5281	Approved
0.7222	Intermediate Similarity	NPD4202	Approved
0.7209	Intermediate Similarity	NPD5363	Approved
0.7191	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD4692	Approved
0.7143	Intermediate Similarity	NPD4139	Approved
0.7126	Intermediate Similarity	NPD5279	Phase 3
0.7065	Intermediate Similarity	NPD5210	Approved
0.7065	Intermediate Similarity	NPD4629	Approved
0.7065	Intermediate Similarity	NPD5695	Phase 3
0.7059	Intermediate Similarity	NPD4270	Approved
0.7059	Intermediate Similarity	NPD4269	Approved
0.7033	Intermediate Similarity	NPD5133	Approved
0.6988	Remote Similarity	NPD3617	Approved
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4788	Approved
0.6974	Remote Similarity	NPD7341	Phase 2
0.6966	Remote Similarity	NPD5208	Approved
0.6962	Remote Similarity	NPD4747	Approved
0.6932	Remote Similarity	NPD3618	Phase 1
0.6915	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD4755	Approved
0.6915	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD4786	Approved
0.6889	Remote Similarity	NPD6080	Approved
0.6889	Remote Similarity	NPD5328	Approved
0.6889	Remote Similarity	NPD6904	Approved
0.6889	Remote Similarity	NPD6673	Approved
0.6875	Remote Similarity	NPD5276	Approved
0.686	Remote Similarity	NPD3667	Approved
0.6842	Remote Similarity	NPD5696	Approved
0.6835	Remote Similarity	NPD4137	Phase 3
0.6824	Remote Similarity	NPD4252	Approved
0.6824	Remote Similarity	NPD4695	Discontinued
0.6824	Remote Similarity	NPD5368	Approved
0.6813	Remote Similarity	NPD5207	Approved
0.6813	Remote Similarity	NPD5692	Phase 3
0.6782	Remote Similarity	NPD5362	Discontinued
0.6771	Remote Similarity	NPD4700	Approved
0.6771	Remote Similarity	NPD5285	Approved
0.6771	Remote Similarity	NPD4696	Approved
0.6771	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD4691	Approved
0.6742	Remote Similarity	NPD4519	Discontinued
0.6742	Remote Similarity	NPD7521	Approved
0.6742	Remote Similarity	NPD7334	Approved
0.6742	Remote Similarity	NPD6409	Approved
0.6742	Remote Similarity	NPD4623	Approved
0.6742	Remote Similarity	NPD5786	Approved
0.6742	Remote Similarity	NPD5330	Approved
0.6742	Remote Similarity	NPD6098	Approved
0.6742	Remote Similarity	NPD7146	Approved
0.6742	Remote Similarity	NPD6684	Approved
0.6739	Remote Similarity	NPD6079	Approved
0.6739	Remote Similarity	NPD5693	Phase 1
0.6739	Remote Similarity	NPD5694	Approved
0.6739	Remote Similarity	NPD6050	Approved
0.6707	Remote Similarity	NPD4687	Approved
0.6707	Remote Similarity	NPD5733	Approved
0.6701	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5091	Approved
0.6633	Remote Similarity	NPD5226	Approved
0.6633	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4633	Approved
0.6596	Remote Similarity	NPD6001	Approved
0.6596	Remote Similarity	NPD5282	Discontinued
0.6593	Remote Similarity	NPD6903	Approved
0.6593	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5174	Approved
0.6566	Remote Similarity	NPD4754	Approved
0.6566	Remote Similarity	NPD5175	Approved
0.6526	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4784	Approved
0.6506	Remote Similarity	NPD4058	Approved
0.6506	Remote Similarity	NPD4785	Approved
0.6505	Remote Similarity	NPD6371	Approved
0.6505	Remote Similarity	NPD4634	Approved
0.65	Remote Similarity	NPD5141	Approved
0.6458	Remote Similarity	NPD4697	Phase 3
0.6458	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5221	Approved
0.6458	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD4819	Approved
0.6437	Remote Similarity	NPD4821	Approved
0.6437	Remote Similarity	NPD4822	Approved
0.6437	Remote Similarity	NPD4820	Approved
0.6436	Remote Similarity	NPD6402	Approved
0.6436	Remote Similarity	NPD4768	Approved
0.6436	Remote Similarity	NPD5739	Approved
0.6436	Remote Similarity	NPD7128	Approved
0.6436	Remote Similarity	NPD4767	Approved
0.6436	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD5275	Approved
0.6429	Remote Similarity	NPD4190	Phase 3
0.6413	Remote Similarity	NPD5737	Approved
0.6413	Remote Similarity	NPD6672	Approved
0.6404	Remote Similarity	NPD5331	Approved
0.6404	Remote Similarity	NPD5332	Approved
0.6392	Remote Similarity	NPD5173	Approved
0.6373	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD857	Phase 3
0.6364	Remote Similarity	NPD4790	Discontinued
0.6354	Remote Similarity	NPD5654	Approved
0.6333	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD6899	Approved
0.6311	Remote Similarity	NPD6881	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6311	Remote Similarity	NPD5128	Approved
0.6311	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.631	Remote Similarity	NPD6926	Approved
0.631	Remote Similarity	NPD6924	Approved
0.6296	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6224	Remote Similarity	NPD5959	Approved
0.6207	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6883	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD7290	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD7102	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5250	Approved
0.6184	Remote Similarity	NPD287	Approved
0.6163	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6933	Approved
0.6132	Remote Similarity	NPD5127	Approved
0.6132	Remote Similarity	NPD5215	Approved
0.6132	Remote Similarity	NPD8130	Phase 1
0.6132	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5216	Approved
0.6132	Remote Similarity	NPD6617	Approved
0.6132	Remote Similarity	NPD6650	Approved
0.6132	Remote Similarity	NPD6847	Approved
0.6132	Remote Similarity	NPD6649	Approved
0.6132	Remote Similarity	NPD6869	Approved
0.6132	Remote Similarity	NPD5217	Approved
0.6111	Remote Similarity	NPD5209	Approved
0.6087	Remote Similarity	NPD1696	Phase 3
0.6087	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6052	Approved
0.6075	Remote Similarity	NPD8297	Approved
0.6075	Remote Similarity	NPD6882	Approved
0.6067	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6412	Phase 2
0.6058	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7154	Phase 3
0.6042	Remote Similarity	NPD7515	Phase 2
0.6036	Remote Similarity	NPD4522	Approved
0.6024	Remote Similarity	NPD6922	Approved
0.6024	Remote Similarity	NPD6923	Approved
0.6019	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1695	Approved
0.5982	Remote Similarity	NPD6059	Approved
0.5982	Remote Similarity	NPD6054	Approved
0.5982	Remote Similarity	NPD6319	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