NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	4.194
LogD:	3.791
LogS:	-4.564
# Rotatable Bonds:	1
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	5.603
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.608
MDCK Permeability:	2.6217830964014865e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.114
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.404
Plasma Protein Binding (PPB):	92.62967681884766%
Volume Distribution (VD):	1.332
Pgp-substrate:	2.942145586013794%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	7.84
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.57
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.855
Carcinogencity:	0.067
Eye Corrosion:	0.073
Eye Irritation:	0.353
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC477089

Natural Product ID:	NPC477089
*Common Name:**	(1R,2S,5E,9E,11R,12S)-1,5,9-trimethyl-12-[(2S)-2-methyloxiran-2-yl]-15-oxabicyclo[9.3.1]pentadeca-5,9-dien-2-ol
IUPAC Name:	(1R,2S,5E,9E,11R,12S)-1,5,9-trimethyl-12-[(2S)-2-methyloxiran-2-yl]-15-oxabicyclo[9.3.1]pentadeca-5,9-dien-2-ol
Synonyms:
Standard InCHIKey:	FVNDVDDHIZTLES-IWONKVGOSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-14-6-5-7-15(2)12-17-16(20(4)13-22-20)10-11-19(3,23-17)18(21)9-8-14/h6,12,16-18,21H,5,7-11,13H2,1-4H3/b14-6+,15-12+/t16-,17+,18-,19+,20+/m0/s1
SMILES:	C/C/1=C\CC/C(=C/[C@@H]2[C@H](CC[C@@](O2)([C@H](CC1)O)C)[C@]3(CO3)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11393053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002012] Oxanes

*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
NPO33592	Eunicea sp.	Species	Plexauridae	Eukaryota	n.a.	Caribbean gorgonian octocoral	n.a.	PMID[19299148]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	15	ug/ml	PMID[19299148]

☑ 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 NPC477089 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	189
0.1-0.2	1503
0.2-0.3	5160
0.3-0.4	13927
0.4-0.5	11177
0.5-0.6	7926
0.6-0.7	2551
0.7-0.8	242
0.8-0.85	17
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8816	High Similarity	NPC476703
0.8784	High Similarity	NPC476709
0.8667	High Similarity	NPC471525
0.8667	High Similarity	NPC190859
0.8625	High Similarity	NPC231601
0.859	High Similarity	NPC476701
0.8442	Intermediate Similarity	NPC236228
0.8442	Intermediate Similarity	NPC170148
0.8442	Intermediate Similarity	NPC256720
0.8356	Intermediate Similarity	NPC259299
0.8243	Intermediate Similarity	NPC305698
0.8148	Intermediate Similarity	NPC474894
0.8133	Intermediate Similarity	NPC304690
0.8133	Intermediate Similarity	NPC329989
0.8133	Intermediate Similarity	NPC74722
0.8133	Intermediate Similarity	NPC239373
0.8118	Intermediate Similarity	NPC248312
0.8095	Intermediate Similarity	NPC255143
0.8026	Intermediate Similarity	NPC129630
0.8025	Intermediate Similarity	NPC474739
0.8	Intermediate Similarity	NPC68119
0.8	Intermediate Similarity	NPC13823
0.7931	Intermediate Similarity	NPC197107
0.7931	Intermediate Similarity	NPC3952
0.7895	Intermediate Similarity	NPC472947
0.7882	Intermediate Similarity	NPC311163
0.7875	Intermediate Similarity	NPC84360
0.7857	Intermediate Similarity	NPC83702
0.7838	Intermediate Similarity	NPC471200
0.7831	Intermediate Similarity	NPC477390
0.7831	Intermediate Similarity	NPC477385
0.7821	Intermediate Similarity	NPC143576
0.7816	Intermediate Similarity	NPC49783
0.7805	Intermediate Similarity	NPC100697
0.7805	Intermediate Similarity	NPC474592
0.7778	Intermediate Similarity	NPC240838
0.7765	Intermediate Similarity	NPC298595
0.7765	Intermediate Similarity	NPC471494
0.7763	Intermediate Similarity	NPC272961
0.7753	Intermediate Similarity	NPC67398
0.7753	Intermediate Similarity	NPC91654
0.7753	Intermediate Similarity	NPC474792
0.7727	Intermediate Similarity	NPC202886
0.7727	Intermediate Similarity	NPC191323
0.7711	Intermediate Similarity	NPC246621
0.7683	Intermediate Similarity	NPC86971
0.7683	Intermediate Similarity	NPC233295
0.7674	Intermediate Similarity	NPC281316
0.7662	Intermediate Similarity	NPC16964
0.7662	Intermediate Similarity	NPC269841
0.766	Intermediate Similarity	NPC214714
0.766	Intermediate Similarity	NPC200672
0.7654	Intermediate Similarity	NPC471454
0.7654	Intermediate Similarity	NPC40049
0.7647	Intermediate Similarity	NPC186155
0.7647	Intermediate Similarity	NPC78673
0.7647	Intermediate Similarity	NPC160517
0.764	Intermediate Similarity	NPC302584
0.7625	Intermediate Similarity	NPC12696
0.7614	Intermediate Similarity	NPC299527
0.7614	Intermediate Similarity	NPC477748
0.7614	Intermediate Similarity	NPC133450
0.7609	Intermediate Similarity	NPC476057
0.7609	Intermediate Similarity	NPC182811
0.7609	Intermediate Similarity	NPC347923
0.7595	Intermediate Similarity	NPC329763
0.7586	Intermediate Similarity	NPC476948
0.7586	Intermediate Similarity	NPC474765
0.7556	Intermediate Similarity	NPC119379
0.7553	Intermediate Similarity	NPC26557
0.7531	Intermediate Similarity	NPC293223
0.7531	Intermediate Similarity	NPC329626
0.7531	Intermediate Similarity	NPC229655
0.7531	Intermediate Similarity	NPC268111
0.7531	Intermediate Similarity	NPC301525
0.7528	Intermediate Similarity	NPC177668
0.7527	Intermediate Similarity	NPC274458
0.7527	Intermediate Similarity	NPC79449
0.7527	Intermediate Similarity	NPC312325
0.7527	Intermediate Similarity	NPC474957
0.75	Intermediate Similarity	NPC103165
0.75	Intermediate Similarity	NPC57664
0.75	Intermediate Similarity	NPC311736
0.75	Intermediate Similarity	NPC267027
0.75	Intermediate Similarity	NPC210717
0.7474	Intermediate Similarity	NPC252242
0.7474	Intermediate Similarity	NPC470972
0.7474	Intermediate Similarity	NPC475956
0.7471	Intermediate Similarity	NPC477387
0.7471	Intermediate Similarity	NPC61527
0.7471	Intermediate Similarity	NPC477389
0.747	Intermediate Similarity	NPC471537
0.7468	Intermediate Similarity	NPC306085
0.7468	Intermediate Similarity	NPC477084
0.7447	Intermediate Similarity	NPC79631
0.7447	Intermediate Similarity	NPC130792
0.7447	Intermediate Similarity	NPC475053
0.7444	Intermediate Similarity	NPC477749
0.7444	Intermediate Similarity	NPC476705
0.7419	Intermediate Similarity	NPC125551
0.7419	Intermediate Similarity	NPC261807
0.7419	Intermediate Similarity	NPC91197
0.7419	Intermediate Similarity	NPC239547
0.7419	Intermediate Similarity	NPC155319
0.7419	Intermediate Similarity	NPC96597
0.7419	Intermediate Similarity	NPC26307
0.7419	Intermediate Similarity	NPC309503
0.7416	Intermediate Similarity	NPC97103
0.7416	Intermediate Similarity	NPC309310
0.7416	Intermediate Similarity	NPC115607
0.7416	Intermediate Similarity	NPC128066
0.7412	Intermediate Similarity	NPC20072
0.7412	Intermediate Similarity	NPC259858
0.7407	Intermediate Similarity	NPC93213
0.7407	Intermediate Similarity	NPC36479
0.7403	Intermediate Similarity	NPC73603
0.7403	Intermediate Similarity	NPC82337
0.7403	Intermediate Similarity	NPC163290
0.7397	Intermediate Similarity	NPC475931
0.7396	Intermediate Similarity	NPC260809
0.7396	Intermediate Similarity	NPC474783
0.7396	Intermediate Similarity	NPC232515
0.7391	Intermediate Similarity	NPC476720
0.7391	Intermediate Similarity	NPC469583
0.7391	Intermediate Similarity	NPC270013
0.7391	Intermediate Similarity	NPC220221
0.7391	Intermediate Similarity	NPC8774
0.7391	Intermediate Similarity	NPC14961
0.7386	Intermediate Similarity	NPC477386
0.7386	Intermediate Similarity	NPC477388
0.7375	Intermediate Similarity	NPC477085
0.7363	Intermediate Similarity	NPC472196
0.7363	Intermediate Similarity	NPC320089
0.7363	Intermediate Similarity	NPC238090
0.7363	Intermediate Similarity	NPC472195
0.7363	Intermediate Similarity	NPC212486
0.7356	Intermediate Similarity	NPC290731
0.7356	Intermediate Similarity	NPC470658
0.7349	Intermediate Similarity	NPC3852
0.7342	Intermediate Similarity	NPC470041
0.734	Intermediate Similarity	NPC222303
0.7333	Intermediate Similarity	NPC473448
0.7326	Intermediate Similarity	NPC23748
0.7326	Intermediate Similarity	NPC49208
0.7326	Intermediate Similarity	NPC471340
0.7317	Intermediate Similarity	NPC469880
0.7317	Intermediate Similarity	NPC271070
0.7312	Intermediate Similarity	NPC472997
0.7312	Intermediate Similarity	NPC472995
0.7312	Intermediate Similarity	NPC227583
0.7312	Intermediate Similarity	NPC476315
0.7312	Intermediate Similarity	NPC72204
0.7312	Intermediate Similarity	NPC12103
0.7312	Intermediate Similarity	NPC472996
0.7312	Intermediate Similarity	NPC98457
0.7312	Intermediate Similarity	NPC90583
0.7303	Intermediate Similarity	NPC309656
0.7303	Intermediate Similarity	NPC476706
0.7303	Intermediate Similarity	NPC476707
0.7303	Intermediate Similarity	NPC476704
0.7303	Intermediate Similarity	NPC281516
0.7297	Intermediate Similarity	NPC127824
0.7294	Intermediate Similarity	NPC5361
0.7294	Intermediate Similarity	NPC471661
0.7292	Intermediate Similarity	NPC475986
0.7283	Intermediate Similarity	NPC159698
0.7283	Intermediate Similarity	NPC256368
0.7283	Intermediate Similarity	NPC474035
0.7283	Intermediate Similarity	NPC81386
0.7283	Intermediate Similarity	NPC65402
0.7283	Intermediate Similarity	NPC127718
0.7273	Intermediate Similarity	NPC476217
0.7273	Intermediate Similarity	NPC470836
0.7273	Intermediate Similarity	NPC247826
0.7263	Intermediate Similarity	NPC272223
0.7262	Intermediate Similarity	NPC139712
0.7262	Intermediate Similarity	NPC325869
0.7253	Intermediate Similarity	NPC184463
0.7253	Intermediate Similarity	NPC30515
0.7253	Intermediate Similarity	NPC158061
0.7253	Intermediate Similarity	NPC114389
0.725	Intermediate Similarity	NPC477087
0.725	Intermediate Similarity	NPC477086
0.7245	Intermediate Similarity	NPC470980
0.7245	Intermediate Similarity	NPC93026
0.7245	Intermediate Similarity	NPC29389
0.7245	Intermediate Similarity	NPC469960
0.7245	Intermediate Similarity	NPC265502
0.7241	Intermediate Similarity	NPC166279
0.7241	Intermediate Similarity	NPC474776
0.7241	Intermediate Similarity	NPC9868
0.7241	Intermediate Similarity	NPC72464
0.7241	Intermediate Similarity	NPC266718
0.7237	Intermediate Similarity	NPC300593
0.7234	Intermediate Similarity	NPC205143
0.7234	Intermediate Similarity	NPC475332
0.7234	Intermediate Similarity	NPC40812
0.7234	Intermediate Similarity	NPC472998
0.7229	Intermediate Similarity	NPC476439
0.7222	Intermediate Similarity	NPC473564

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 NPC477089 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1965
0.2-0.3	3883
0.3-0.4	2200
0.4-0.5	706
0.5-0.6	178
0.6-0.7	46
0.7-0.8	5
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
0.7931	Intermediate Similarity	NPD46	Approved
0.7931	Intermediate Similarity	NPD6698	Approved
0.7727	Intermediate Similarity	NPD7838	Discovery
0.7553	Intermediate Similarity	NPD5344	Discontinued
0.7191	Intermediate Similarity	NPD7524	Approved
0.7083	Intermediate Similarity	NPD6648	Approved
0.7045	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD368	Approved
0.6932	Remote Similarity	NPD6695	Phase 3
0.6804	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6931	Approved
0.6782	Remote Similarity	NPD6930	Phase 2
0.6774	Remote Similarity	NPD3168	Discontinued
0.6765	Remote Similarity	NPD6686	Approved
0.6709	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6933	Approved
0.6702	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6635	Remote Similarity	NPD6371	Approved
0.663	Remote Similarity	NPD7750	Discontinued
0.6591	Remote Similarity	NPD7514	Phase 3
0.6591	Remote Similarity	NPD7332	Phase 2
0.6571	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6902	Approved
0.6505	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD6926	Approved
0.6437	Remote Similarity	NPD5776	Phase 2
0.6437	Remote Similarity	NPD6925	Approved
0.6437	Remote Similarity	NPD6932	Approved
0.6413	Remote Similarity	NPD6893	Approved
0.6413	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.64	Remote Similarity	NPD342	Phase 1
0.6381	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD371	Approved
0.6374	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD7145	Approved
0.6364	Remote Similarity	NPD7327	Approved
0.6354	Remote Similarity	NPD7087	Discontinued
0.6333	Remote Similarity	NPD6898	Phase 1
0.6316	Remote Similarity	NPD1695	Approved
0.6306	Remote Similarity	NPD7516	Approved
0.63	Remote Similarity	NPD4225	Approved
0.63	Remote Similarity	NPD7638	Approved
0.6292	Remote Similarity	NPD6683	Phase 2
0.6292	Remote Similarity	NPD7645	Phase 2
0.6289	Remote Similarity	NPD5778	Approved
0.6289	Remote Similarity	NPD5779	Approved
0.6277	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD6640	Phase 3
0.625	Remote Similarity	NPD8377	Approved
0.625	Remote Similarity	NPD5357	Phase 1
0.6238	Remote Similarity	NPD7640	Approved
0.6238	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD5282	Discontinued
0.6222	Remote Similarity	NPD4822	Approved
0.6222	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD4821	Approved
0.6222	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4819	Approved
0.6222	Remote Similarity	NPD7525	Registered
0.6222	Remote Similarity	NPD7509	Discontinued
0.6207	Remote Similarity	NPD8264	Approved
0.6195	Remote Similarity	NPD8378	Approved
0.6195	Remote Similarity	NPD8033	Approved
0.6195	Remote Similarity	NPD8296	Approved
0.6195	Remote Similarity	NPD8335	Approved
0.6195	Remote Similarity	NPD8380	Approved
0.6195	Remote Similarity	NPD8379	Approved
0.6195	Remote Similarity	NPD7503	Approved
0.619	Remote Similarity	NPD6412	Phase 2
0.618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4159	Approved
0.617	Remote Similarity	NPD4249	Approved
0.6163	Remote Similarity	NPD4732	Discontinued
0.6154	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8273	Phase 1
0.6117	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6053	Discontinued
0.6053	Remote Similarity	NPD8515	Approved
0.6053	Remote Similarity	NPD8516	Approved
0.6053	Remote Similarity	NPD8517	Approved
0.6053	Remote Similarity	NPD8513	Phase 3
0.6023	Remote Similarity	NPD7339	Approved
0.6023	Remote Similarity	NPD6942	Approved
0.6022	Remote Similarity	NPD7154	Phase 3
0.602	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6923	Approved
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD6922	Approved
0.6	Remote Similarity	NPD4271	Approved
0.5983	Remote Similarity	NPD7507	Approved
0.5982	Remote Similarity	NPD7115	Discovery
0.5981	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6101	Approved
0.5979	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7839	Suspended
0.593	Remote Similarity	NPD7143	Approved
0.593	Remote Similarity	NPD7144	Approved
0.5918	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6435	Approved
0.5862	Remote Similarity	NPD7151	Approved
0.5862	Remote Similarity	NPD7150	Approved
0.5862	Remote Similarity	NPD7152	Approved
0.5859	Remote Similarity	NPD6411	Approved
0.5856	Remote Similarity	NPD8133	Approved
0.5851	Remote Similarity	NPD5362	Discontinued
0.5833	Remote Similarity	NPD7319	Approved
0.5816	Remote Similarity	NPD6051	Approved
0.5812	Remote Similarity	NPD7829	Approved
0.5812	Remote Similarity	NPD7642	Approved
0.5812	Remote Similarity	NPD7830	Approved
0.5802	Remote Similarity	NPD1145	Discontinued
0.5798	Remote Similarity	NPD8074	Phase 3
0.5747	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5126	Approved
0.5726	Remote Similarity	NPD5125	Phase 3
0.5714	Remote Similarity	NPD8451	Approved
0.5702	Remote Similarity	NPD7505	Discontinued
0.5699	Remote Similarity	NPD5368	Approved
0.5686	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5332	Approved
0.5684	Remote Similarity	NPD5331	Approved
0.5682	Remote Similarity	NPD4243	Approved
0.5667	Remote Similarity	NPD8039	Approved
0.5667	Remote Similarity	NPD8448	Approved
0.566	Remote Similarity	NPD7632	Discontinued
0.5652	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD7331	Phase 2
0.5641	Remote Similarity	NPD8444	Approved
0.5638	Remote Similarity	NPD5369	Approved
0.5638	Remote Similarity	NPD4790	Discontinued
0.5636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4786	Approved
0.5616	Remote Similarity	NPD4265	Approved
0.56	Remote Similarity	NPD7136	Phase 2
0.56	Remote Similarity	NPD5785	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