NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.635
LogD:	2.455
LogS:	-3.683
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.207
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:	-4.641
MDCK Permeability:	2.7517655325937085e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	76.19913482666016%
Volume Distribution (VD):	1.31
Pgp-substrate:	26.290489196777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.761
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	5.393
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.396
Carcinogencity:	0.027
Eye Corrosion:	0.944
Eye Irritation:	0.988
Respiratory Toxicity:	0.82

Download Data

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

Natural Product: NPC185874

Natural Product ID:	NPC185874
*Common Name:**	Cyperusol C
IUPAC Name:	(1R,4R,4aR,6R,8aR)-4,8a-dimethyl-6-prop-1-en-2-yl-1,2,3,4a,5,6,7,8-octahydronaphthalene-1,4-diol
Synonyms:	Cyperusol C
Standard InCHIKey:	LGKGTMWCBFNQHP-KJWHEZOQSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3)12(9-11)15(4,17)8-6-13(14)16/h11-13,16-17H,1,5-9H2,2-4H3/t11-,12-,13-,14-,15-/m1/s1
SMILES:	CC(=C)[C@@H]1CC[C@@]2([C@@H](C1)[C@](C)(O)CC[C@H]2O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465340
PubChem CID:	11230158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO7630	Cyperus longus	Species	Cyperaceae	Eukaryota	n.a.	Egyptian herbal medicine	n.a.	PMID[15104485]
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]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23387824]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7630	Cyperus longus	Species	Cyperaceae	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
EC50	1
IC50	6
Others	7

Activity Type	# Activity
Cell Line	11
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	29.9	%	PMID[535979]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	28.4	%	PMID[535979]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	8.1	%	PMID[535979]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	6.3	%	PMID[535979]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[535980]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[535980]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[535980]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[535980]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[535980]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	420200.0	nM	PMID[535980]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[535980]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	65.0	%	PMID[535981]
NPT27	Others	Unspecified		Ratio CC50/EC50	>	2.8	n.a.	PMID[535980]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	150400.0	nM	PMID[535980]

☑ 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 NPC185874 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	195
0.1-0.2	2203
0.2-0.3	9507
0.3-0.4	15661
0.4-0.5	6297
0.5-0.6	5551
0.6-0.7	2612
0.7-0.8	582
0.8-0.85	59
0.85-0.9	15
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC139207
0.9516	High Similarity	NPC101128
0.9375	High Similarity	NPC253303
0.9375	High Similarity	NPC269077
0.9365	High Similarity	NPC11555
0.9365	High Similarity	NPC282619
0.9365	High Similarity	NPC2728
0.9365	High Similarity	NPC208198
0.9365	High Similarity	NPC172613
0.9365	High Similarity	NPC60837
0.9231	High Similarity	NPC244790
0.9206	High Similarity	NPC144650
0.9104	High Similarity	NPC164022
0.9062	High Similarity	NPC258595
0.8971	High Similarity	NPC95165
0.8939	High Similarity	NPC245795
0.8939	High Similarity	NPC276616
0.8923	High Similarity	NPC473929
0.8906	High Similarity	NPC68656
0.8824	High Similarity	NPC167706
0.8714	High Similarity	NPC3403
0.871	High Similarity	NPC474769
0.871	High Similarity	NPC189290
0.8676	High Similarity	NPC283316
0.8676	High Similarity	NPC92801
0.8636	High Similarity	NPC475897
0.8592	High Similarity	NPC63958
0.8529	High Similarity	NPC210323
0.8529	High Similarity	NPC234511
0.8529	High Similarity	NPC9942
0.8429	Intermediate Similarity	NPC211009
0.8406	Intermediate Similarity	NPC45296
0.8387	Intermediate Similarity	NPC264779
0.8382	Intermediate Similarity	NPC2648
0.8382	Intermediate Similarity	NPC266578
0.8356	Intermediate Similarity	NPC301707
0.8333	Intermediate Similarity	NPC14112
0.8333	Intermediate Similarity	NPC219940
0.8333	Intermediate Similarity	NPC91573
0.8333	Intermediate Similarity	NPC86305
0.831	Intermediate Similarity	NPC201048
0.831	Intermediate Similarity	NPC476366
0.831	Intermediate Similarity	NPC308440
0.831	Intermediate Similarity	NPC472503
0.8286	Intermediate Similarity	NPC23954
0.8286	Intermediate Similarity	NPC111234
0.8286	Intermediate Similarity	NPC471272
0.8286	Intermediate Similarity	NPC301226
0.8254	Intermediate Similarity	NPC236588
0.8243	Intermediate Similarity	NPC273410
0.8243	Intermediate Similarity	NPC80530
0.8226	Intermediate Similarity	NPC471269
0.8219	Intermediate Similarity	NPC470711
0.8219	Intermediate Similarity	NPC138502
0.8219	Intermediate Similarity	NPC470758
0.8209	Intermediate Similarity	NPC64123
0.8194	Intermediate Similarity	NPC212879
0.8194	Intermediate Similarity	NPC240235
0.8194	Intermediate Similarity	NPC70982
0.8194	Intermediate Similarity	NPC291503
0.8194	Intermediate Similarity	NPC185536
0.8194	Intermediate Similarity	NPC178383
0.8194	Intermediate Similarity	NPC144075
0.8194	Intermediate Similarity	NPC230704
0.8194	Intermediate Similarity	NPC231256
0.8194	Intermediate Similarity	NPC104387
0.8169	Intermediate Similarity	NPC182717
0.8169	Intermediate Similarity	NPC68443
0.8133	Intermediate Similarity	NPC322313
0.8133	Intermediate Similarity	NPC236237
0.8133	Intermediate Similarity	NPC102253
0.8108	Intermediate Similarity	NPC472342
0.8108	Intermediate Similarity	NPC477819
0.8108	Intermediate Similarity	NPC285761
0.8108	Intermediate Similarity	NPC472501
0.8108	Intermediate Similarity	NPC6978
0.8108	Intermediate Similarity	NPC31828
0.8108	Intermediate Similarity	NPC138621
0.8108	Intermediate Similarity	NPC167037
0.8108	Intermediate Similarity	NPC244385
0.8108	Intermediate Similarity	NPC42853
0.8108	Intermediate Similarity	NPC300499
0.8108	Intermediate Similarity	NPC477817
0.8088	Intermediate Similarity	NPC476406
0.8082	Intermediate Similarity	NPC470766
0.8082	Intermediate Similarity	NPC278091
0.8082	Intermediate Similarity	NPC106432
0.8082	Intermediate Similarity	NPC167873
0.8082	Intermediate Similarity	NPC265588
0.8082	Intermediate Similarity	NPC38141
0.8082	Intermediate Similarity	NPC78067
0.8082	Intermediate Similarity	NPC1973
0.8082	Intermediate Similarity	NPC470749
0.8082	Intermediate Similarity	NPC93662
0.8056	Intermediate Similarity	NPC91858
0.8056	Intermediate Similarity	NPC49168
0.8056	Intermediate Similarity	NPC62657
0.8056	Intermediate Similarity	NPC100334
0.8056	Intermediate Similarity	NPC192638
0.8056	Intermediate Similarity	NPC25511
0.8056	Intermediate Similarity	NPC5046
0.8056	Intermediate Similarity	NPC476736
0.8056	Intermediate Similarity	NPC145552
0.8056	Intermediate Similarity	NPC243342
0.8056	Intermediate Similarity	NPC196358
0.8056	Intermediate Similarity	NPC254509
0.8056	Intermediate Similarity	NPC477138
0.8052	Intermediate Similarity	NPC243347
0.8052	Intermediate Similarity	NPC470929
0.8028	Intermediate Similarity	NPC242992
0.8	Intermediate Similarity	NPC49599
0.8	Intermediate Similarity	NPC49627
0.8	Intermediate Similarity	NPC291379
0.8	Intermediate Similarity	NPC24504
0.7973	Intermediate Similarity	NPC90979
0.7973	Intermediate Similarity	NPC257191
0.7973	Intermediate Similarity	NPC119355
0.7973	Intermediate Similarity	NPC202540
0.7973	Intermediate Similarity	NPC34177
0.7973	Intermediate Similarity	NPC471798
0.7973	Intermediate Similarity	NPC169994
0.7973	Intermediate Similarity	NPC40394
0.7973	Intermediate Similarity	NPC157996
0.7973	Intermediate Similarity	NPC101475
0.7973	Intermediate Similarity	NPC472805
0.7973	Intermediate Similarity	NPC331618
0.7973	Intermediate Similarity	NPC260301
0.7973	Intermediate Similarity	NPC130136
0.7973	Intermediate Similarity	NPC307336
0.7973	Intermediate Similarity	NPC248830
0.7973	Intermediate Similarity	NPC212241
0.7969	Intermediate Similarity	NPC135438
0.7945	Intermediate Similarity	NPC66566
0.7945	Intermediate Similarity	NPC477923
0.7945	Intermediate Similarity	NPC32832
0.7945	Intermediate Similarity	NPC200243
0.7941	Intermediate Similarity	NPC300442
0.7937	Intermediate Similarity	NPC84824
0.7937	Intermediate Similarity	NPC67508
0.7917	Intermediate Similarity	NPC220939
0.7917	Intermediate Similarity	NPC471799
0.7917	Intermediate Similarity	NPC195489
0.7917	Intermediate Similarity	NPC265485
0.7895	Intermediate Similarity	NPC71535
0.7895	Intermediate Similarity	NPC13554
0.7895	Intermediate Similarity	NPC78545
0.7895	Intermediate Similarity	NPC47149
0.7895	Intermediate Similarity	NPC475679
0.7867	Intermediate Similarity	NPC98386
0.7867	Intermediate Similarity	NPC474989
0.7867	Intermediate Similarity	NPC196753
0.7867	Intermediate Similarity	NPC22955
0.7867	Intermediate Similarity	NPC158662
0.7867	Intermediate Similarity	NPC475
0.7867	Intermediate Similarity	NPC472499
0.7867	Intermediate Similarity	NPC253807
0.7867	Intermediate Similarity	NPC102708
0.7867	Intermediate Similarity	NPC470396
0.7867	Intermediate Similarity	NPC472500
0.7867	Intermediate Similarity	NPC99168
0.7867	Intermediate Similarity	NPC230295
0.7867	Intermediate Similarity	NPC472502
0.7857	Intermediate Similarity	NPC94192
0.7857	Intermediate Similarity	NPC208999
0.7857	Intermediate Similarity	NPC96484
0.7857	Intermediate Similarity	NPC471238
0.7838	Intermediate Similarity	NPC120098
0.7838	Intermediate Similarity	NPC265328
0.7838	Intermediate Similarity	NPC477925
0.7838	Intermediate Similarity	NPC189883
0.7838	Intermediate Similarity	NPC274079
0.7838	Intermediate Similarity	NPC30590
0.7838	Intermediate Similarity	NPC290598
0.7838	Intermediate Similarity	NPC73875
0.7838	Intermediate Similarity	NPC27765
0.7838	Intermediate Similarity	NPC122418
0.7838	Intermediate Similarity	NPC237460
0.7821	Intermediate Similarity	NPC211135
0.7821	Intermediate Similarity	NPC85095
0.7821	Intermediate Similarity	NPC216420
0.7821	Intermediate Similarity	NPC207013
0.7821	Intermediate Similarity	NPC232023
0.7812	Intermediate Similarity	NPC39068
0.7808	Intermediate Similarity	NPC71152
0.7808	Intermediate Similarity	NPC471797
0.7808	Intermediate Similarity	NPC306727
0.7794	Intermediate Similarity	NPC225415
0.7792	Intermediate Similarity	NPC476646
0.7792	Intermediate Similarity	NPC157655
0.7778	Intermediate Similarity	NPC242001
0.7778	Intermediate Similarity	NPC110799
0.7778	Intermediate Similarity	NPC477792
0.7763	Intermediate Similarity	NPC470429
0.7763	Intermediate Similarity	NPC53744
0.7763	Intermediate Similarity	NPC80297
0.7763	Intermediate Similarity	NPC475727
0.7763	Intermediate Similarity	NPC472463
0.7763	Intermediate Similarity	NPC472742
0.7763	Intermediate Similarity	NPC476316
0.7763	Intermediate Similarity	NPC5604

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 NPC185874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	2700
0.2-0.3	4027
0.3-0.4	1630
0.4-0.5	305
0.5-0.6	198
0.6-0.7	115
0.7-0.8	9
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
0.8133	Intermediate Similarity	NPD7525	Registered
0.7763	Intermediate Similarity	NPD7645	Phase 2
0.76	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6942	Approved
0.7467	Intermediate Similarity	NPD7339	Approved
0.7333	Intermediate Similarity	NPD6924	Approved
0.7333	Intermediate Similarity	NPD6926	Approved
0.7215	Intermediate Similarity	NPD7509	Discontinued
0.7195	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6933	Approved
0.7108	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD368	Approved
0.7	Intermediate Similarity	NPD4748	Discontinued
0.6935	Remote Similarity	NPD385	Approved
0.6935	Remote Similarity	NPD384	Approved
0.6867	Remote Similarity	NPD4786	Approved
0.686	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD7150	Approved
0.6842	Remote Similarity	NPD7152	Approved
0.6842	Remote Similarity	NPD7151	Approved
0.6842	Remote Similarity	NPD4243	Approved
0.6824	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6922	Approved
0.68	Remote Similarity	NPD6923	Approved
0.6795	Remote Similarity	NPD8264	Approved
0.679	Remote Similarity	NPD6931	Approved
0.679	Remote Similarity	NPD6930	Phase 2
0.6747	Remote Similarity	NPD4788	Approved
0.6711	Remote Similarity	NPD4787	Phase 1
0.6711	Remote Similarity	NPD7143	Approved
0.6711	Remote Similarity	NPD7144	Approved
0.6705	Remote Similarity	NPD6079	Approved
0.6705	Remote Similarity	NPD7515	Phase 2
0.6705	Remote Similarity	NPD8035	Phase 2
0.6705	Remote Similarity	NPD8034	Phase 2
0.6703	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6625	Remote Similarity	NPD6932	Approved
0.6582	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD5275	Approved
0.6579	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD371	Approved
0.6559	Remote Similarity	NPD4700	Approved
0.6559	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD5285	Approved
0.6559	Remote Similarity	NPD5286	Approved
0.6548	Remote Similarity	NPD6695	Phase 3
0.6543	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5223	Approved
0.6463	Remote Similarity	NPD6683	Phase 2
0.6463	Remote Similarity	NPD4195	Approved
0.6421	Remote Similarity	NPD5224	Approved
0.6421	Remote Similarity	NPD5226	Approved
0.6421	Remote Similarity	NPD5211	Phase 2
0.6421	Remote Similarity	NPD4633	Approved
0.6421	Remote Similarity	NPD5225	Approved
0.642	Remote Similarity	NPD5776	Phase 2
0.642	Remote Similarity	NPD6925	Approved
0.642	Remote Similarity	NPD6116	Phase 1
0.6413	Remote Similarity	NPD5222	Approved
0.6413	Remote Similarity	NPD5221	Approved
0.6413	Remote Similarity	NPD4697	Phase 3
0.6413	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6893	Approved
0.6389	Remote Similarity	NPD1145	Discontinued
0.6386	Remote Similarity	NPD7332	Phase 2
0.6386	Remote Similarity	NPD7514	Phase 3
0.6375	Remote Similarity	NPD3703	Phase 2
0.6374	Remote Similarity	NPD7748	Approved
0.6354	Remote Similarity	NPD4754	Approved
0.6354	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD5175	Approved
0.6344	Remote Similarity	NPD5173	Approved
0.6344	Remote Similarity	NPD7902	Approved
0.6341	Remote Similarity	NPD7145	Approved
0.631	Remote Similarity	NPD6898	Phase 1
0.6296	Remote Similarity	NPD6117	Approved
0.6292	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD5141	Approved
0.6279	Remote Similarity	NPD3668	Phase 3
0.6277	Remote Similarity	NPD7638	Approved
0.6277	Remote Similarity	NPD5290	Discontinued
0.6267	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD388	Approved
0.625	Remote Similarity	NPD7750	Discontinued
0.625	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD386	Approved
0.6235	Remote Similarity	NPD4223	Phase 3
0.6235	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD6675	Approved
0.6224	Remote Similarity	NPD5739	Approved
0.6224	Remote Similarity	NPD6402	Approved
0.6224	Remote Similarity	NPD4767	Approved
0.6224	Remote Similarity	NPD7128	Approved
0.6224	Remote Similarity	NPD4768	Approved
0.6211	Remote Similarity	NPD7639	Approved
0.6211	Remote Similarity	NPD7640	Approved
0.6162	Remote Similarity	NPD5697	Approved
0.6162	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD3698	Phase 2
0.6145	Remote Similarity	NPD6115	Approved
0.6145	Remote Similarity	NPD6118	Approved
0.6145	Remote Similarity	NPD6114	Approved
0.6145	Remote Similarity	NPD6697	Approved
0.6143	Remote Similarity	NPD342	Phase 1
0.6136	Remote Similarity	NPD5279	Phase 3
0.6136	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6902	Approved
0.6105	Remote Similarity	NPD4225	Approved
0.61	Remote Similarity	NPD4730	Approved
0.61	Remote Similarity	NPD6011	Approved
0.61	Remote Similarity	NPD6881	Approved
0.61	Remote Similarity	NPD5128	Approved
0.61	Remote Similarity	NPD6899	Approved
0.61	Remote Similarity	NPD7320	Approved
0.61	Remote Similarity	NPD4729	Approved
0.6092	Remote Similarity	NPD4197	Approved
0.6076	Remote Similarity	NPD4245	Approved
0.6076	Remote Similarity	NPD4244	Approved
0.604	Remote Similarity	NPD6014	Approved
0.604	Remote Similarity	NPD6373	Approved
0.604	Remote Similarity	NPD6372	Approved
0.604	Remote Similarity	NPD6013	Approved
0.604	Remote Similarity	NPD6012	Approved
0.6026	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD5360	Phase 3
0.6023	Remote Similarity	NPD5329	Approved
0.6022	Remote Similarity	NPD7900	Approved
0.6022	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD4695	Discontinued
0.598	Remote Similarity	NPD5169	Approved
0.598	Remote Similarity	NPD5251	Approved
0.598	Remote Similarity	NPD5250	Approved
0.598	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6883	Approved
0.598	Remote Similarity	NPD5135	Approved
0.598	Remote Similarity	NPD7290	Approved
0.598	Remote Similarity	NPD5247	Approved
0.598	Remote Similarity	NPD5248	Approved
0.598	Remote Similarity	NPD4634	Approved
0.598	Remote Similarity	NPD7102	Approved
0.598	Remote Similarity	NPD5249	Phase 3
0.5979	Remote Similarity	NPD4159	Approved
0.5978	Remote Similarity	NPD7087	Discontinued
0.5957	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD4629	Approved
0.5955	Remote Similarity	NPD4138	Approved
0.5955	Remote Similarity	NPD4623	Approved
0.5955	Remote Similarity	NPD5205	Approved
0.5955	Remote Similarity	NPD4519	Discontinued
0.5955	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD4690	Approved
0.5955	Remote Similarity	NPD4688	Approved
0.5955	Remote Similarity	NPD4693	Phase 3
0.5952	Remote Similarity	NPD3617	Approved
0.5952	Remote Similarity	NPD3671	Phase 1
0.5941	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6847	Approved
0.5922	Remote Similarity	NPD8130	Phase 1
0.5922	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6649	Approved
0.5922	Remote Similarity	NPD5217	Approved
0.5922	Remote Similarity	NPD6869	Approved
0.5922	Remote Similarity	NPD6617	Approved
0.5922	Remote Similarity	NPD5216	Approved
0.5922	Remote Similarity	NPD5215	Approved
0.5922	Remote Similarity	NPD6650	Approved
0.5922	Remote Similarity	NPD5127	Approved
0.5889	Remote Similarity	NPD3573	Approved
0.5882	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4789	Approved
0.587	Remote Similarity	NPD3168	Discontinued
0.5865	Remote Similarity	NPD8297	Approved
0.5865	Remote Similarity	NPD6882	Approved
0.5854	Remote Similarity	NPD1810	Approved
0.5854	Remote Similarity	NPD1811	Approved
0.5843	Remote Similarity	NPD1696	Phase 3
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5824	Remote Similarity	NPD4723	Approved
0.5824	Remote Similarity	NPD4722	Approved
0.5823	Remote Similarity	NPD6705	Phase 1
0.581	Remote Similarity	NPD4632	Approved
0.5802	Remote Similarity	NPD4758	Discontinued
0.5784	Remote Similarity	NPD5168	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