NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.47
LogD:	2.66
LogS:	-3.097
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	4.307
Fsp3:	0.867
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:	-4.464
MDCK Permeability:	1.8757409634417854e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.129
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	55.90451431274414%
Volume Distribution (VD):	0.841
Pgp-substrate:	44.06707000732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.585
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.487
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	8.85
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.119
Carcinogencity:	0.087
Eye Corrosion:	0.149
Eye Irritation:	0.928
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC219940

Natural Product ID:	NPC219940
*Common Name:**	Oppsit-4(15)-Ene-1Beta,11-Diol
IUPAC Name:	(1R,3aR,4R,7aS)-1-(2-hydroxy-2-methylpropyl)-3a-methyl-7-methylidene-2,3,4,5,6,7a-hexahydro-1H-inden-4-ol
Synonyms:
Standard InCHIKey:	UACKNRNYUIAHPT-BHPKHCPMSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10-5-6-12(16)15(4)8-7-11(13(10)15)9-14(2,3)17/h11-13,16-17H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m1/s1
SMILES:	C=C1CC[C@H]([C@]2(C)CC[C@H](CC(C)(C)O)[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814428
PubChem CID:	56672124
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
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]

☑ 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
EC50	1
IC50	6
Others	1

Activity Type	# Activity
Cell Line	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[493034]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[493034]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[493034]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[493034]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[493034]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	420200.0	nM	PMID[493034]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[493034]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	420200.0	nM	PMID[493034]

☑ 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 NPC219940 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	125
0.1-0.2	2036
0.2-0.3	13333
0.3-0.4	12279
0.4-0.5	6498
0.5-0.6	5833
0.6-0.7	2108
0.7-0.8	453
0.8-0.85	30
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9508	High Similarity	NPC300442
0.873	High Similarity	NPC101128
0.8551	High Similarity	NPC3403
0.8438	Intermediate Similarity	NPC144650
0.8429	Intermediate Similarity	NPC91573
0.8413	Intermediate Similarity	NPC147524
0.8382	Intermediate Similarity	NPC111234
0.8333	Intermediate Similarity	NPC269077
0.8333	Intermediate Similarity	NPC308522
0.8333	Intermediate Similarity	NPC74885
0.8333	Intermediate Similarity	NPC253303
0.8333	Intermediate Similarity	NPC185874
0.8333	Intermediate Similarity	NPC139207
0.8308	Intermediate Similarity	NPC172613
0.8308	Intermediate Similarity	NPC208198
0.8308	Intermediate Similarity	NPC2728
0.8308	Intermediate Similarity	NPC282619
0.8308	Intermediate Similarity	NPC60837
0.8308	Intermediate Similarity	NPC258595
0.8308	Intermediate Similarity	NPC11555
0.8286	Intermediate Similarity	NPC185536
0.8286	Intermediate Similarity	NPC212879
0.8286	Intermediate Similarity	NPC230704
0.8286	Intermediate Similarity	NPC231256
0.8286	Intermediate Similarity	NPC104387
0.8286	Intermediate Similarity	NPC240235
0.8286	Intermediate Similarity	NPC70982
0.8286	Intermediate Similarity	NPC178383
0.8235	Intermediate Similarity	NPC45296
0.8209	Intermediate Similarity	NPC244790
0.8194	Intermediate Similarity	NPC31828
0.8194	Intermediate Similarity	NPC42853
0.8194	Intermediate Similarity	NPC472342
0.8194	Intermediate Similarity	NPC285761
0.8194	Intermediate Similarity	NPC301707
0.8169	Intermediate Similarity	NPC73875
0.8169	Intermediate Similarity	NPC278091
0.8169	Intermediate Similarity	NPC86305
0.8169	Intermediate Similarity	NPC78067
0.8169	Intermediate Similarity	NPC14112
0.8169	Intermediate Similarity	NPC93662
0.8154	Intermediate Similarity	NPC225415
0.8143	Intermediate Similarity	NPC329090
0.8143	Intermediate Similarity	NPC49168
0.8143	Intermediate Similarity	NPC254509
0.8143	Intermediate Similarity	NPC25511
0.8143	Intermediate Similarity	NPC27395
0.8143	Intermediate Similarity	NPC62657
0.8143	Intermediate Similarity	NPC145552
0.8143	Intermediate Similarity	NPC5046
0.8143	Intermediate Similarity	NPC196358
0.8143	Intermediate Similarity	NPC308440
0.8143	Intermediate Similarity	NPC192638
0.8143	Intermediate Similarity	NPC472503
0.8082	Intermediate Similarity	NPC80530
0.8082	Intermediate Similarity	NPC49627
0.8082	Intermediate Similarity	NPC49599
0.8082	Intermediate Similarity	NPC273410
0.8056	Intermediate Similarity	NPC214570
0.8056	Intermediate Similarity	NPC212241
0.8056	Intermediate Similarity	NPC331618
0.8056	Intermediate Similarity	NPC257191
0.8056	Intermediate Similarity	NPC202540
0.8056	Intermediate Similarity	NPC119355
0.8056	Intermediate Similarity	NPC248830
0.8033	Intermediate Similarity	NPC84824
0.8033	Intermediate Similarity	NPC67508
0.8028	Intermediate Similarity	NPC322353
0.8028	Intermediate Similarity	NPC118508
0.8028	Intermediate Similarity	NPC200243
0.8028	Intermediate Similarity	NPC328104
0.8028	Intermediate Similarity	NPC319090
0.8028	Intermediate Similarity	NPC121744
0.8	Intermediate Similarity	NPC474140
0.8	Intermediate Similarity	NPC195489
0.7973	Intermediate Similarity	NPC322313
0.7973	Intermediate Similarity	NPC13554
0.7973	Intermediate Similarity	NPC102253
0.7973	Intermediate Similarity	NPC236237
0.7971	Intermediate Similarity	NPC283316
0.7945	Intermediate Similarity	NPC167037
0.7945	Intermediate Similarity	NPC275910
0.7945	Intermediate Similarity	NPC477819
0.7945	Intermediate Similarity	NPC244385
0.7945	Intermediate Similarity	NPC477817
0.7945	Intermediate Similarity	NPC6978
0.7945	Intermediate Similarity	NPC102708
0.7945	Intermediate Similarity	NPC472501
0.7945	Intermediate Similarity	NPC138621
0.7941	Intermediate Similarity	NPC245795
0.7941	Intermediate Similarity	NPC276616
0.7937	Intermediate Similarity	NPC189290
0.7937	Intermediate Similarity	NPC474769
0.7917	Intermediate Similarity	NPC315261
0.7917	Intermediate Similarity	NPC189883
0.7917	Intermediate Similarity	NPC237460
0.7917	Intermediate Similarity	NPC202642
0.7917	Intermediate Similarity	NPC46160
0.791	Intermediate Similarity	NPC473929
0.7887	Intermediate Similarity	NPC476736
0.7887	Intermediate Similarity	NPC199316
0.7887	Intermediate Similarity	NPC309178
0.7887	Intermediate Similarity	NPC102313
0.7879	Intermediate Similarity	NPC68656
0.7857	Intermediate Similarity	NPC164022
0.7857	Intermediate Similarity	NPC167706
0.7846	Intermediate Similarity	NPC185547
0.7846	Intermediate Similarity	NPC95804
0.7838	Intermediate Similarity	NPC1319
0.7838	Intermediate Similarity	NPC80297
0.7838	Intermediate Similarity	NPC472742
0.7838	Intermediate Similarity	NPC475727
0.7838	Intermediate Similarity	NPC116119
0.7826	Intermediate Similarity	NPC9942
0.7808	Intermediate Similarity	NPC198968
0.7808	Intermediate Similarity	NPC260301
0.7808	Intermediate Similarity	NPC318495
0.7808	Intermediate Similarity	NPC155986
0.7808	Intermediate Similarity	NPC307336
0.7808	Intermediate Similarity	NPC138502
0.7808	Intermediate Similarity	NPC31037
0.7794	Intermediate Similarity	NPC136813
0.7778	Intermediate Similarity	NPC103822
0.7778	Intermediate Similarity	NPC471723
0.7778	Intermediate Similarity	NPC257347
0.7778	Intermediate Similarity	NPC141071
0.7778	Intermediate Similarity	NPC313185
0.7763	Intermediate Similarity	NPC218616
0.7763	Intermediate Similarity	NPC296701
0.7763	Intermediate Similarity	NPC87489
0.7763	Intermediate Similarity	NPC30166
0.7761	Intermediate Similarity	NPC477009
0.7761	Intermediate Similarity	NPC238352
0.7761	Intermediate Similarity	NPC476737
0.7761	Intermediate Similarity	NPC27243
0.7746	Intermediate Similarity	NPC95165
0.7746	Intermediate Similarity	NPC14352
0.7746	Intermediate Similarity	NPC472506
0.7746	Intermediate Similarity	NPC201373
0.7746	Intermediate Similarity	NPC234527
0.7733	Intermediate Similarity	NPC78545
0.7733	Intermediate Similarity	NPC475679
0.7733	Intermediate Similarity	NPC71535
0.7733	Intermediate Similarity	NPC236112
0.7733	Intermediate Similarity	NPC206735
0.7714	Intermediate Similarity	NPC133873
0.7714	Intermediate Similarity	NPC92801
0.7703	Intermediate Similarity	NPC472499
0.7703	Intermediate Similarity	NPC302041
0.7703	Intermediate Similarity	NPC205455
0.7703	Intermediate Similarity	NPC475
0.7703	Intermediate Similarity	NPC186191
0.7703	Intermediate Similarity	NPC65897
0.7703	Intermediate Similarity	NPC85346
0.7703	Intermediate Similarity	NPC472500
0.7703	Intermediate Similarity	NPC472502
0.7692	Intermediate Similarity	NPC135648
0.7681	Intermediate Similarity	NPC266578
0.7681	Intermediate Similarity	NPC160209
0.7681	Intermediate Similarity	NPC167527
0.7671	Intermediate Similarity	NPC240604
0.7671	Intermediate Similarity	NPC300324
0.7671	Intermediate Similarity	NPC129165
0.7671	Intermediate Similarity	NPC38141
0.7671	Intermediate Similarity	NPC134330
0.7671	Intermediate Similarity	NPC107059
0.7671	Intermediate Similarity	NPC321381
0.7671	Intermediate Similarity	NPC321016
0.7671	Intermediate Similarity	NPC470362
0.7662	Intermediate Similarity	NPC85095
0.7662	Intermediate Similarity	NPC470929
0.7662	Intermediate Similarity	NPC211135
0.7662	Intermediate Similarity	NPC207013
0.7662	Intermediate Similarity	NPC232023
0.7662	Intermediate Similarity	NPC216420
0.7647	Intermediate Similarity	NPC475897
0.7647	Intermediate Similarity	NPC476406
0.7639	Intermediate Similarity	NPC469593
0.7639	Intermediate Similarity	NPC469534
0.7639	Intermediate Similarity	NPC469533
0.7632	Intermediate Similarity	NPC474531
0.7632	Intermediate Similarity	NPC6707
0.7619	Intermediate Similarity	NPC39068
0.7619	Intermediate Similarity	NPC264779
0.7612	Intermediate Similarity	NPC309300
0.7606	Intermediate Similarity	NPC469343
0.7606	Intermediate Similarity	NPC471272
0.7606	Intermediate Similarity	NPC477792
0.7606	Intermediate Similarity	NPC164045
0.76	Intermediate Similarity	NPC24504
0.76	Intermediate Similarity	NPC476316
0.76	Intermediate Similarity	NPC30986
0.76	Intermediate Similarity	NPC229204
0.76	Intermediate Similarity	NPC209430
0.76	Intermediate Similarity	NPC328714
0.76	Intermediate Similarity	NPC5604
0.7571	Intermediate Similarity	NPC475952
0.7571	Intermediate Similarity	NPC269877
0.7571	Intermediate Similarity	NPC210323
0.7571	Intermediate Similarity	NPC234511

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 NPC219940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	2666
0.2-0.3	4320
0.3-0.4	1421
0.4-0.5	280
0.5-0.6	217
0.6-0.7	99
0.7-0.8	24
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD6924	Approved
0.8143	Intermediate Similarity	NPD6926	Approved
0.7973	Intermediate Similarity	NPD7525	Registered
0.7917	Intermediate Similarity	NPD6933	Approved
0.7571	Intermediate Similarity	NPD6923	Approved
0.7571	Intermediate Similarity	NPD6922	Approved
0.7534	Intermediate Similarity	NPD6942	Approved
0.7534	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD7509	Discontinued
0.75	Intermediate Similarity	NPD6930	Phase 2
0.7465	Intermediate Similarity	NPD7143	Approved
0.7465	Intermediate Similarity	NPD7144	Approved
0.7432	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6929	Approved
0.7361	Intermediate Similarity	NPD7150	Approved
0.7361	Intermediate Similarity	NPD7151	Approved
0.7361	Intermediate Similarity	NPD7152	Approved
0.7333	Intermediate Similarity	NPD6932	Approved
0.7273	Intermediate Similarity	NPD4748	Discontinued
0.725	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6695	Phase 3
0.7143	Intermediate Similarity	NPD6683	Phase 2
0.7125	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4243	Approved
0.7105	Intermediate Similarity	NPD6925	Approved
0.7105	Intermediate Similarity	NPD5776	Phase 2
0.7083	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7514	Phase 3
0.7037	Intermediate Similarity	NPD6893	Approved
0.7013	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7145	Approved
0.7	Intermediate Similarity	NPD4788	Approved
0.7	Intermediate Similarity	NPD385	Approved
0.7	Intermediate Similarity	NPD384	Approved
0.6951	Remote Similarity	NPD3618	Phase 1
0.6933	Remote Similarity	NPD4785	Approved
0.6933	Remote Similarity	NPD4784	Approved
0.6923	Remote Similarity	NPD7645	Phase 2
0.6914	Remote Similarity	NPD4786	Approved
0.6905	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD3667	Approved
0.6867	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7524	Approved
0.6867	Remote Similarity	NPD7750	Discontinued
0.686	Remote Similarity	NPD4202	Approved
0.6842	Remote Similarity	NPD5275	Approved
0.6842	Remote Similarity	NPD4190	Phase 3
0.6835	Remote Similarity	NPD7332	Phase 2
0.6812	Remote Similarity	NPD368	Approved
0.6757	Remote Similarity	NPD4787	Phase 1
0.675	Remote Similarity	NPD6902	Approved
0.675	Remote Similarity	NPD6898	Phase 1
0.6747	Remote Similarity	NPD5279	Phase 3
0.6744	Remote Similarity	NPD6079	Approved
0.6709	Remote Similarity	NPD4195	Approved
0.6707	Remote Similarity	NPD3133	Approved
0.6707	Remote Similarity	NPD3665	Phase 1
0.6707	Remote Similarity	NPD3666	Approved
0.6556	Remote Similarity	NPD4755	Approved
0.6552	Remote Similarity	NPD8034	Phase 2
0.6552	Remote Similarity	NPD7087	Discontinued
0.6552	Remote Similarity	NPD8035	Phase 2
0.6528	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4753	Phase 2
0.6463	Remote Similarity	NPD4223	Phase 3
0.6463	Remote Similarity	NPD4221	Approved
0.6447	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4697	Phase 3
0.6444	Remote Similarity	NPD5221	Approved
0.6444	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD1145	Discontinued
0.6413	Remote Similarity	NPD4700	Approved
0.6413	Remote Similarity	NPD5285	Approved
0.6413	Remote Similarity	NPD4696	Approved
0.6413	Remote Similarity	NPD5286	Approved
0.641	Remote Similarity	NPD8264	Approved
0.64	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5173	Approved
0.6344	Remote Similarity	NPD5223	Approved
0.6329	Remote Similarity	NPD6117	Approved
0.631	Remote Similarity	NPD4197	Approved
0.6282	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5211	Phase 2
0.6277	Remote Similarity	NPD5225	Approved
0.6277	Remote Similarity	NPD4633	Approved
0.6277	Remote Similarity	NPD5224	Approved
0.6277	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD6116	Phase 1
0.6235	Remote Similarity	NPD5329	Approved
0.6211	Remote Similarity	NPD4754	Approved
0.6211	Remote Similarity	NPD5175	Approved
0.6211	Remote Similarity	NPD5174	Approved
0.6203	Remote Similarity	NPD3703	Phase 2
0.6184	Remote Similarity	NPD3698	Phase 2
0.6176	Remote Similarity	NPD342	Phase 1
0.6173	Remote Similarity	NPD6118	Approved
0.6173	Remote Similarity	NPD6114	Approved
0.6173	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6697	Approved
0.6173	Remote Similarity	NPD6115	Approved
0.6163	Remote Similarity	NPD5280	Approved
0.6163	Remote Similarity	NPD4138	Approved
0.6163	Remote Similarity	NPD4690	Approved
0.6163	Remote Similarity	NPD4693	Phase 3
0.6163	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4688	Approved
0.6163	Remote Similarity	NPD5205	Approved
0.6163	Remote Similarity	NPD4694	Approved
0.6163	Remote Similarity	NPD5690	Phase 2
0.6163	Remote Similarity	NPD4689	Approved
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6146	Remote Similarity	NPD5141	Approved
0.6145	Remote Similarity	NPD4692	Approved
0.6145	Remote Similarity	NPD4139	Approved
0.6129	Remote Similarity	NPD5290	Discontinued
0.6129	Remote Similarity	NPD7638	Approved
0.6118	Remote Similarity	NPD3668	Phase 3
0.6111	Remote Similarity	NPD6399	Phase 3
0.6104	Remote Similarity	NPD4789	Approved
0.6104	Remote Similarity	NPD4244	Approved
0.6104	Remote Similarity	NPD4245	Approved
0.6082	Remote Similarity	NPD6402	Approved
0.6082	Remote Similarity	NPD7128	Approved
0.6082	Remote Similarity	NPD4767	Approved
0.6082	Remote Similarity	NPD5739	Approved
0.6082	Remote Similarity	NPD4768	Approved
0.6082	Remote Similarity	NPD6675	Approved
0.6064	Remote Similarity	NPD7640	Approved
0.6064	Remote Similarity	NPD7639	Approved
0.6053	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6705	Phase 1
0.6053	Remote Similarity	NPD5360	Phase 3
0.6032	Remote Similarity	NPD386	Approved
0.6032	Remote Similarity	NPD388	Approved
0.6023	Remote Similarity	NPD4722	Approved
0.6023	Remote Similarity	NPD4723	Approved
0.6022	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD6084	Phase 2
0.602	Remote Similarity	NPD5697	Approved
0.602	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD7515	Phase 2
0.5978	Remote Similarity	NPD5695	Phase 3
0.5976	Remote Similarity	NPD3617	Approved
0.596	Remote Similarity	NPD4729	Approved
0.596	Remote Similarity	NPD6011	Approved
0.596	Remote Similarity	NPD5128	Approved
0.596	Remote Similarity	NPD7320	Approved
0.596	Remote Similarity	NPD6881	Approved
0.596	Remote Similarity	NPD6899	Approved
0.596	Remote Similarity	NPD4730	Approved
0.5955	Remote Similarity	NPD6051	Approved
0.5946	Remote Similarity	NPD371	Approved
0.59	Remote Similarity	NPD6012	Approved
0.59	Remote Similarity	NPD6373	Approved
0.59	Remote Similarity	NPD6014	Approved
0.59	Remote Similarity	NPD6013	Approved
0.59	Remote Similarity	NPD6372	Approved
0.5889	Remote Similarity	NPD4096	Approved
0.5889	Remote Similarity	NPD7136	Phase 2
0.5843	Remote Similarity	NPD4518	Approved
0.5842	Remote Similarity	NPD5248	Approved
0.5842	Remote Similarity	NPD5169	Approved
0.5842	Remote Similarity	NPD5249	Phase 3
0.5842	Remote Similarity	NPD5251	Approved
0.5842	Remote Similarity	NPD6883	Approved
0.5842	Remote Similarity	NPD5247	Approved
0.5842	Remote Similarity	NPD5135	Approved
0.5842	Remote Similarity	NPD7102	Approved
0.5842	Remote Similarity	NPD7290	Approved
0.5842	Remote Similarity	NPD5250	Approved
0.5842	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4634	Approved
0.5833	Remote Similarity	NPD4822	Approved
0.5833	Remote Similarity	NPD4819	Approved
0.5833	Remote Similarity	NPD4820	Approved
0.5833	Remote Similarity	NPD6928	Phase 2
0.5833	Remote Similarity	NPD4821	Approved
0.5833	Remote Similarity	NPD4159	Approved
0.5824	Remote Similarity	NPD5281	Approved
0.5824	Remote Similarity	NPD5284	Approved
0.5823	Remote Similarity	NPD4758	Discontinued
0.5814	Remote Similarity	NPD5332	Approved
0.5814	Remote Similarity	NPD5362	Discontinued
0.5814	Remote Similarity	NPD5331	Approved
0.5802	Remote Similarity	NPD3702	Approved
0.58	Remote Similarity	NPD5168	Approved
0.5795	Remote Similarity	NPD6409	Approved
0.5795	Remote Similarity	NPD7146	Approved
0.5795	Remote Similarity	NPD7334	Approved
0.5795	Remote Similarity	NPD6684	Approved
0.5795	Remote Similarity	NPD5330	Approved
0.5795	Remote Similarity	NPD7521	Approved
0.5789	Remote Similarity	NPD4225	Approved
0.5789	Remote Similarity	NPD5696	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