NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	248.481
LogP:	3.603
LogD:	4.175
LogS:	-4.437
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	5.575
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.507
MDCK Permeability:	2.619806218717713e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.726
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.346

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	59.501670837402344%
Volume Distribution (VD):	1.139
Pgp-substrate:	41.91043472290039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.544
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	15.537
Half-life (T1/2):	0.489

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.103
Carcinogencity:	0.073
Eye Corrosion:	0.517
Eye Irritation:	0.125
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC473929

Natural Product ID:	NPC473929
*Common Name:**	Cervicol
IUPAC Name:	n.a.
Synonyms:	Cervicol
Standard InCHIKey:	DATKFZMVDXINEI-UJOWSUJOSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-8(2)10-5-6-15(4)13-9(3)7-11(16)14(15)12(10)13/h8,10-14,16H,3,5-7H2,1-2,4H3/t10-,11-,12+,13-,14+,15-/m0/s1
SMILES:	CC(C)C1CCC2(C3C1C2C(=C)CC3O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455489
PubChem CID:	44584341
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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO33357	lemnalia carvicorni	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	uM	PMID[450459]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	uM	PMID[450459]

☑ 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 NPC473929 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	237
0.1-0.2	2509
0.2-0.3	11359
0.3-0.4	15252
0.4-0.5	5756
0.5-0.6	5044
0.6-0.7	2029
0.7-0.8	464
0.8-0.85	43
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC475897
0.9355	High Similarity	NPC144650
0.9206	High Similarity	NPC172613
0.9206	High Similarity	NPC208198
0.9206	High Similarity	NPC2728
0.9206	High Similarity	NPC11555
0.9206	High Similarity	NPC282619
0.9206	High Similarity	NPC60837
0.9048	High Similarity	NPC101128
0.9048	High Similarity	NPC68656
0.8923	High Similarity	NPC139207
0.8923	High Similarity	NPC269077
0.8923	High Similarity	NPC185874
0.8923	High Similarity	NPC253303
0.8788	High Similarity	NPC276616
0.8788	High Similarity	NPC244790
0.8615	High Similarity	NPC258595
0.8551	High Similarity	NPC95165
0.8548	High Similarity	NPC189290
0.8548	High Similarity	NPC474769
0.8529	High Similarity	NPC45296
0.8529	High Similarity	NPC92801
0.8507	High Similarity	NPC245795
0.8406	Intermediate Similarity	NPC167706
0.8406	Intermediate Similarity	NPC111234
0.8406	Intermediate Similarity	NPC301226
0.8361	Intermediate Similarity	NPC67508
0.8361	Intermediate Similarity	NPC84824
0.8286	Intermediate Similarity	NPC182717
0.8286	Intermediate Similarity	NPC211009
0.8261	Intermediate Similarity	NPC283316
0.8235	Intermediate Similarity	NPC208999
0.8226	Intermediate Similarity	NPC264779
0.8197	Intermediate Similarity	NPC53209
0.8169	Intermediate Similarity	NPC477138
0.8169	Intermediate Similarity	NPC254509
0.8169	Intermediate Similarity	NPC62657
0.8169	Intermediate Similarity	NPC49168
0.8169	Intermediate Similarity	NPC243342
0.8169	Intermediate Similarity	NPC25511
0.8169	Intermediate Similarity	NPC145552
0.8169	Intermediate Similarity	NPC5046
0.8169	Intermediate Similarity	NPC472503
0.8169	Intermediate Similarity	NPC196358
0.8169	Intermediate Similarity	NPC308440
0.8169	Intermediate Similarity	NPC192638
0.8169	Intermediate Similarity	NPC100334
0.8143	Intermediate Similarity	NPC164022
0.8116	Intermediate Similarity	NPC9942
0.8116	Intermediate Similarity	NPC210323
0.8116	Intermediate Similarity	NPC474248
0.8082	Intermediate Similarity	NPC471798
0.806	Intermediate Similarity	NPC64123
0.8056	Intermediate Similarity	NPC144075
0.8056	Intermediate Similarity	NPC477923
0.8056	Intermediate Similarity	NPC3403
0.8056	Intermediate Similarity	NPC240235
0.8056	Intermediate Similarity	NPC70982
0.8056	Intermediate Similarity	NPC178383
0.8056	Intermediate Similarity	NPC212879
0.8056	Intermediate Similarity	NPC230704
0.8056	Intermediate Similarity	NPC200243
0.8056	Intermediate Similarity	NPC66566
0.8056	Intermediate Similarity	NPC231256
0.8056	Intermediate Similarity	NPC185536
0.8056	Intermediate Similarity	NPC104387
0.8056	Intermediate Similarity	NPC291503
0.8028	Intermediate Similarity	NPC195489
0.8028	Intermediate Similarity	NPC471799
0.8	Intermediate Similarity	NPC145498
0.7973	Intermediate Similarity	NPC470396
0.7973	Intermediate Similarity	NPC474989
0.7973	Intermediate Similarity	NPC99168
0.7973	Intermediate Similarity	NPC22955
0.7971	Intermediate Similarity	NPC266578
0.7971	Intermediate Similarity	NPC2648
0.7971	Intermediate Similarity	NPC96484
0.7945	Intermediate Similarity	NPC106364
0.7945	Intermediate Similarity	NPC189883
0.7945	Intermediate Similarity	NPC91573
0.7945	Intermediate Similarity	NPC93662
0.7945	Intermediate Similarity	NPC300324
0.7945	Intermediate Similarity	NPC120098
0.7945	Intermediate Similarity	NPC14112
0.7945	Intermediate Similarity	NPC78067
0.7945	Intermediate Similarity	NPC63958
0.7945	Intermediate Similarity	NPC278091
0.7945	Intermediate Similarity	NPC86305
0.7945	Intermediate Similarity	NPC290598
0.7945	Intermediate Similarity	NPC30590
0.7945	Intermediate Similarity	NPC27765
0.7945	Intermediate Similarity	NPC122418
0.7945	Intermediate Similarity	NPC265328
0.7945	Intermediate Similarity	NPC237460
0.7945	Intermediate Similarity	NPC240604
0.7945	Intermediate Similarity	NPC265588
0.7917	Intermediate Similarity	NPC471797
0.7917	Intermediate Similarity	NPC201048
0.7917	Intermediate Similarity	NPC91858
0.7917	Intermediate Similarity	NPC476366
0.791	Intermediate Similarity	NPC219940
0.791	Intermediate Similarity	NPC225415
0.7887	Intermediate Similarity	NPC477792
0.7887	Intermediate Similarity	NPC242001
0.7887	Intermediate Similarity	NPC110799
0.7887	Intermediate Similarity	NPC242992
0.7867	Intermediate Similarity	NPC472463
0.7867	Intermediate Similarity	NPC53744
0.7867	Intermediate Similarity	NPC291379
0.7857	Intermediate Similarity	NPC234511
0.7838	Intermediate Similarity	NPC248830
0.7838	Intermediate Similarity	NPC212241
0.7838	Intermediate Similarity	NPC34177
0.7838	Intermediate Similarity	NPC138502
0.7838	Intermediate Similarity	NPC119355
0.7838	Intermediate Similarity	NPC91594
0.7838	Intermediate Similarity	NPC260301
0.7838	Intermediate Similarity	NPC331618
0.7838	Intermediate Similarity	NPC257191
0.7838	Intermediate Similarity	NPC202540
0.7838	Intermediate Similarity	NPC477924
0.7838	Intermediate Similarity	NPC470711
0.7838	Intermediate Similarity	NPC90979
0.7838	Intermediate Similarity	NPC157996
0.7838	Intermediate Similarity	NPC472805
0.7838	Intermediate Similarity	NPC101475
0.7838	Intermediate Similarity	NPC470758
0.7838	Intermediate Similarity	NPC307336
0.7838	Intermediate Similarity	NPC40394
0.7826	Intermediate Similarity	NPC171225
0.7808	Intermediate Similarity	NPC230301
0.7808	Intermediate Similarity	NPC162742
0.7808	Intermediate Similarity	NPC288035
0.7808	Intermediate Similarity	NPC471723
0.7808	Intermediate Similarity	NPC322353
0.7808	Intermediate Similarity	NPC34700
0.7808	Intermediate Similarity	NPC136188
0.7808	Intermediate Similarity	NPC141071
0.7808	Intermediate Similarity	NPC28657
0.7808	Intermediate Similarity	NPC285893
0.7808	Intermediate Similarity	NPC257347
0.7808	Intermediate Similarity	NPC121744
0.7808	Intermediate Similarity	NPC118508
0.7808	Intermediate Similarity	NPC22105
0.7808	Intermediate Similarity	NPC134847
0.7808	Intermediate Similarity	NPC304309
0.7808	Intermediate Similarity	NPC138374
0.7794	Intermediate Similarity	NPC27243
0.7794	Intermediate Similarity	NPC476737
0.7794	Intermediate Similarity	NPC300442
0.7778	Intermediate Similarity	NPC220939
0.7778	Intermediate Similarity	NPC68443
0.7778	Intermediate Similarity	NPC265485
0.7763	Intermediate Similarity	NPC47149
0.7763	Intermediate Similarity	NPC71535
0.7763	Intermediate Similarity	NPC78545
0.7733	Intermediate Similarity	NPC196753
0.7733	Intermediate Similarity	NPC253807
0.7733	Intermediate Similarity	NPC244385
0.7733	Intermediate Similarity	NPC6978
0.7733	Intermediate Similarity	NPC302041
0.7733	Intermediate Similarity	NPC31828
0.7733	Intermediate Similarity	NPC285761
0.7733	Intermediate Similarity	NPC167037
0.7733	Intermediate Similarity	NPC42853
0.7733	Intermediate Similarity	NPC472499
0.7733	Intermediate Similarity	NPC472501
0.7733	Intermediate Similarity	NPC301707
0.7733	Intermediate Similarity	NPC230295
0.7733	Intermediate Similarity	NPC477819
0.7733	Intermediate Similarity	NPC300499
0.7733	Intermediate Similarity	NPC477817
0.7733	Intermediate Similarity	NPC85346
0.7733	Intermediate Similarity	NPC158662
0.7733	Intermediate Similarity	NPC275910
0.7733	Intermediate Similarity	NPC102708
0.7733	Intermediate Similarity	NPC65897
0.7733	Intermediate Similarity	NPC472500
0.7733	Intermediate Similarity	NPC312328
0.7733	Intermediate Similarity	NPC98386
0.7733	Intermediate Similarity	NPC472342
0.7733	Intermediate Similarity	NPC138621
0.7714	Intermediate Similarity	NPC94192
0.7703	Intermediate Similarity	NPC113733
0.7703	Intermediate Similarity	NPC38141
0.7703	Intermediate Similarity	NPC477925
0.7703	Intermediate Similarity	NPC321381
0.7703	Intermediate Similarity	NPC129165
0.7703	Intermediate Similarity	NPC106432
0.7703	Intermediate Similarity	NPC274079
0.7703	Intermediate Similarity	NPC202642
0.7703	Intermediate Similarity	NPC96319
0.7703	Intermediate Similarity	NPC470766
0.7703	Intermediate Similarity	NPC107059
0.7703	Intermediate Similarity	NPC73875
0.7703	Intermediate Similarity	NPC134330
0.7703	Intermediate Similarity	NPC321016
0.7703	Intermediate Similarity	NPC470749
0.7703	Intermediate Similarity	NPC46160
0.7681	Intermediate Similarity	NPC476406

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 NPC473929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2782
0.2-0.3	4073
0.3-0.4	1506
0.4-0.5	282
0.5-0.6	199
0.6-0.7	69
0.7-0.8	6
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
0.7808	Intermediate Similarity	NPD7339	Approved
0.7808	Intermediate Similarity	NPD6942	Approved
0.7703	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7645	Phase 2
0.7532	Intermediate Similarity	NPD7525	Registered
0.72	Intermediate Similarity	NPD6924	Approved
0.72	Intermediate Similarity	NPD6926	Approved
0.7162	Intermediate Similarity	NPD7150	Approved
0.7162	Intermediate Similarity	NPD7151	Approved
0.7162	Intermediate Similarity	NPD7152	Approved
0.7125	Intermediate Similarity	NPD3667	Approved
0.7123	Intermediate Similarity	NPD6923	Approved
0.7123	Intermediate Similarity	NPD6922	Approved
0.7073	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD385	Approved
0.7049	Intermediate Similarity	NPD384	Approved
0.7027	Intermediate Similarity	NPD7143	Approved
0.7027	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD6933	Approved
0.6988	Remote Similarity	NPD3618	Phase 1
0.6951	Remote Similarity	NPD4786	Approved
0.6883	Remote Similarity	NPD8264	Approved
0.6875	Remote Similarity	NPD4748	Discontinued
0.6875	Remote Similarity	NPD7509	Discontinued
0.6753	Remote Similarity	NPD4784	Approved
0.6753	Remote Similarity	NPD4785	Approved
0.675	Remote Similarity	NPD6929	Approved
0.6744	Remote Similarity	NPD5328	Approved
0.6711	Remote Similarity	NPD4243	Approved
0.6706	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7515	Phase 2
0.6591	Remote Similarity	NPD6079	Approved
0.6548	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD3666	Approved
0.6548	Remote Similarity	NPD3665	Phase 1
0.6517	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD5776	Phase 2
0.65	Remote Similarity	NPD6925	Approved
0.65	Remote Similarity	NPD6932	Approved
0.6456	Remote Similarity	NPD5275	Approved
0.6456	Remote Similarity	NPD4190	Phase 3
0.6447	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4788	Approved
0.6429	Remote Similarity	NPD6695	Phase 3
0.642	Remote Similarity	NPD7145	Approved
0.642	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8034	Phase 2
0.6404	Remote Similarity	NPD8035	Phase 2
0.6389	Remote Similarity	NPD368	Approved
0.6364	Remote Similarity	NPD4787	Phase 1
0.6353	Remote Similarity	NPD3668	Phase 3
0.6353	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6683	Phase 2
0.6304	Remote Similarity	NPD5222	Approved
0.6304	Remote Similarity	NPD4697	Phase 3
0.6304	Remote Similarity	NPD5221	Approved
0.6304	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6893	Approved
0.6265	Remote Similarity	NPD7332	Phase 2
0.6265	Remote Similarity	NPD7514	Phase 3
0.6264	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD3703	Phase 2
0.6237	Remote Similarity	NPD5173	Approved
0.6237	Remote Similarity	NPD4755	Approved
0.6232	Remote Similarity	NPD342	Phase 1
0.619	Remote Similarity	NPD6902	Approved
0.619	Remote Similarity	NPD6898	Phase 1
0.6173	Remote Similarity	NPD6117	Approved
0.617	Remote Similarity	NPD4225	Approved
0.617	Remote Similarity	NPD5290	Discontinued
0.617	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6145	Remote Similarity	NPD4195	Approved
0.6136	Remote Similarity	NPD7750	Discontinued
0.6136	Remote Similarity	NPD7524	Approved
0.6133	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4700	Approved
0.6105	Remote Similarity	NPD5286	Approved
0.6105	Remote Similarity	NPD5285	Approved
0.6105	Remote Similarity	NPD7639	Approved
0.6105	Remote Similarity	NPD4696	Approved
0.6105	Remote Similarity	NPD7640	Approved
0.6098	Remote Similarity	NPD6116	Phase 1
0.6071	Remote Similarity	NPD4695	Discontinued
0.6064	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD5223	Approved
0.6027	Remote Similarity	NPD1145	Discontinued
0.6026	Remote Similarity	NPD3698	Phase 2
0.6024	Remote Similarity	NPD6114	Approved
0.6024	Remote Similarity	NPD6115	Approved
0.6024	Remote Similarity	NPD6118	Approved
0.6024	Remote Similarity	NPD6697	Approved
0.6023	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD371	Approved
0.5979	Remote Similarity	NPD5225	Approved
0.5979	Remote Similarity	NPD4633	Approved
0.5979	Remote Similarity	NPD5226	Approved
0.5979	Remote Similarity	NPD5224	Approved
0.5979	Remote Similarity	NPD5211	Phase 2
0.5949	Remote Similarity	NPD4245	Approved
0.5949	Remote Similarity	NPD4244	Approved
0.593	Remote Similarity	NPD4221	Approved
0.593	Remote Similarity	NPD4223	Phase 3
0.5918	Remote Similarity	NPD5174	Approved
0.5918	Remote Similarity	NPD4754	Approved
0.5918	Remote Similarity	NPD5175	Approved
0.5876	Remote Similarity	NPD4159	Approved
0.5873	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7087	Discontinued
0.5859	Remote Similarity	NPD5141	Approved
0.5846	Remote Similarity	NPD388	Approved
0.5846	Remote Similarity	NPD386	Approved
0.5843	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3671	Phase 1
0.5833	Remote Similarity	NPD3617	Approved
0.5821	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4768	Approved
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD4767	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5795	Remote Similarity	NPD4197	Approved
0.575	Remote Similarity	NPD4789	Approved
0.5745	Remote Similarity	NPD7900	Approved
0.5745	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5697	Approved
0.5743	Remote Similarity	NPD5701	Approved
0.573	Remote Similarity	NPD1696	Phase 3
0.573	Remote Similarity	NPD5329	Approved
0.5699	Remote Similarity	NPD6411	Approved
0.5698	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD6928	Phase 2
0.5696	Remote Similarity	NPD6705	Phase 1
0.5696	Remote Similarity	NPD5360	Phase 3
0.5696	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD5128	Approved
0.5686	Remote Similarity	NPD4730	Approved
0.5686	Remote Similarity	NPD7320	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.5686	Remote Similarity	NPD5168	Approved
0.5686	Remote Similarity	NPD6011	Approved
0.5686	Remote Similarity	NPD4729	Approved
0.5684	Remote Similarity	NPD5210	Approved
0.5684	Remote Similarity	NPD4629	Approved
0.5667	Remote Similarity	NPD4689	Approved
0.5667	Remote Similarity	NPD4693	Phase 3
0.5667	Remote Similarity	NPD5205	Approved
0.5667	Remote Similarity	NPD4690	Approved
0.5667	Remote Similarity	NPD7521	Approved
0.5667	Remote Similarity	NPD4138	Approved
0.5667	Remote Similarity	NPD6684	Approved
0.5667	Remote Similarity	NPD4519	Discontinued
0.5667	Remote Similarity	NPD7146	Approved
0.5667	Remote Similarity	NPD5330	Approved
0.5667	Remote Similarity	NPD4623	Approved
0.5667	Remote Similarity	NPD7334	Approved
0.5667	Remote Similarity	NPD6409	Approved
0.5667	Remote Similarity	NPD4688	Approved
0.5657	Remote Similarity	NPD7632	Discontinued
0.5631	Remote Similarity	NPD6372	Approved
0.5631	Remote Similarity	NPD6014	Approved
0.5631	Remote Similarity	NPD6013	Approved
0.5631	Remote Similarity	NPD6012	Approved
0.5631	Remote Similarity	NPD6373	Approved
0.5604	Remote Similarity	NPD3573	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