NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	2.644
LogD:	2.205
LogS:	-3.293
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	4.429
Fsp3:	0.733
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:	-4.777
MDCK Permeability:	8.08452932687942e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.898
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.347
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	56.74824523925781%
Volume Distribution (VD):	1.374
Pgp-substrate:	45.25755310058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.645
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	8.881
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.035
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC477792

Natural Product ID:	NPC477792
*Common Name:**	godotol B
IUPAC Name:	(3R,7R)-4,4,5-trimethyl-9-methylidene-2,3,4a,7,8,9a-hexahydro-1H-benzo[7]annulene-3,7-diol
Synonyms:
Standard InCHIKey:	BQBQOPFBRCPZOA-NELGMTEASA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-9-7-11(16)8-10(2)14-12(9)5-6-13(17)15(14,3)4/h8,11-14,16-17H,1,5-7H2,2-4H3/t11-,12?,13-,14?/m1/s1
SMILES:	CC1=C[C@@H](CC(=C)C2C1C([C@@H](CC2)O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11736505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO33598	Pluchea arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568792]

☑ 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
MIC	1
Others	2

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	<	10	%	PMID[15568792]
NPT140	Organism	Artemia	Artemia	LC50	=	540	ug/ml	PMID[15568792]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	500	ug/ml	PMID[15568792]

☑ 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 NPC477792 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	164
0.1-0.2	1438
0.2-0.3	5871
0.3-0.4	16024
0.4-0.5	9825
0.5-0.6	6072
0.6-0.7	2593
0.7-0.8	639
0.8-0.85	51
0.85-0.9	18
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC471238
0.8857	High Similarity	NPC471271
0.8857	High Similarity	NPC471272
0.8857	High Similarity	NPC471268
0.8732	High Similarity	NPC265485
0.8732	High Similarity	NPC220939
0.8714	High Similarity	NPC92801
0.8696	High Similarity	NPC96484
0.863	High Similarity	NPC265588
0.8611	High Similarity	NPC201048
0.8611	High Similarity	NPC476366
0.8611	High Similarity	NPC306727
0.8592	High Similarity	NPC23954
0.8514	High Similarity	NPC470711
0.8514	High Similarity	NPC470758
0.8514	High Similarity	NPC91594
0.8451	Intermediate Similarity	NPC34834
0.8421	Intermediate Similarity	NPC96362
0.8406	Intermediate Similarity	NPC202017
0.84	Intermediate Similarity	NPC476314
0.8382	Intermediate Similarity	NPC225415
0.8382	Intermediate Similarity	NPC144650
0.8378	Intermediate Similarity	NPC253190
0.8378	Intermediate Similarity	NPC470749
0.8356	Intermediate Similarity	NPC243342
0.8356	Intermediate Similarity	NPC477138
0.8333	Intermediate Similarity	NPC164022
0.8333	Intermediate Similarity	NPC167706
0.8312	Intermediate Similarity	NPC159148
0.8312	Intermediate Similarity	NPC476646
0.831	Intermediate Similarity	NPC474248
0.8286	Intermediate Similarity	NPC68703
0.8286	Intermediate Similarity	NPC69649
0.8286	Intermediate Similarity	NPC114651
0.8261	Intermediate Similarity	NPC287339
0.8243	Intermediate Similarity	NPC291503
0.8243	Intermediate Similarity	NPC477923
0.8243	Intermediate Similarity	NPC32832
0.8243	Intermediate Similarity	NPC66566
0.8235	Intermediate Similarity	NPC83200
0.8182	Intermediate Similarity	NPC295131
0.8182	Intermediate Similarity	NPC281880
0.8169	Intermediate Similarity	NPC167527
0.8169	Intermediate Similarity	NPC208999
0.8169	Intermediate Similarity	NPC276616
0.8158	Intermediate Similarity	NPC167891
0.8158	Intermediate Similarity	NPC83351
0.8158	Intermediate Similarity	NPC11908
0.8143	Intermediate Similarity	NPC326310
0.8116	Intermediate Similarity	NPC290367
0.8116	Intermediate Similarity	NPC68656
0.8116	Intermediate Similarity	NPC96793
0.8116	Intermediate Similarity	NPC323424
0.8108	Intermediate Similarity	NPC91858
0.8082	Intermediate Similarity	NPC242992
0.8082	Intermediate Similarity	NPC242001
0.8077	Intermediate Similarity	NPC471270
0.8077	Intermediate Similarity	NPC249423
0.8056	Intermediate Similarity	NPC9942
0.8056	Intermediate Similarity	NPC473893
0.8056	Intermediate Similarity	NPC471560
0.8052	Intermediate Similarity	NPC209430
0.8052	Intermediate Similarity	NPC109546
0.8052	Intermediate Similarity	NPC28862
0.8052	Intermediate Similarity	NPC81306
0.8052	Intermediate Similarity	NPC84694
0.8052	Intermediate Similarity	NPC47982
0.8052	Intermediate Similarity	NPC143182
0.8052	Intermediate Similarity	NPC30986
0.8028	Intermediate Similarity	NPC171225
0.8028	Intermediate Similarity	NPC136813
0.8026	Intermediate Similarity	NPC149550
0.8026	Intermediate Similarity	NPC85105
0.8026	Intermediate Similarity	NPC477924
0.8026	Intermediate Similarity	NPC472805
0.8026	Intermediate Similarity	NPC471798
0.8026	Intermediate Similarity	NPC90979
0.8	Intermediate Similarity	NPC69383
0.8	Intermediate Similarity	NPC171148
0.8	Intermediate Similarity	NPC46320
0.8	Intermediate Similarity	NPC313185
0.8	Intermediate Similarity	NPC60837
0.8	Intermediate Similarity	NPC11555
0.8	Intermediate Similarity	NPC208198
0.8	Intermediate Similarity	NPC258595
0.8	Intermediate Similarity	NPC282619
0.8	Intermediate Similarity	NPC313179
0.8	Intermediate Similarity	NPC133580
0.8	Intermediate Similarity	NPC172613
0.8	Intermediate Similarity	NPC2728
0.7975	Intermediate Similarity	NPC202389
0.7975	Intermediate Similarity	NPC296701
0.7975	Intermediate Similarity	NPC101462
0.7975	Intermediate Similarity	NPC155521
0.7975	Intermediate Similarity	NPC87489
0.7975	Intermediate Similarity	NPC49964
0.7975	Intermediate Similarity	NPC218616
0.7973	Intermediate Similarity	NPC471799
0.7973	Intermediate Similarity	NPC68443
0.7973	Intermediate Similarity	NPC182717
0.7971	Intermediate Similarity	NPC81615
0.7949	Intermediate Similarity	NPC148685
0.7949	Intermediate Similarity	NPC471266
0.7949	Intermediate Similarity	NPC206062
0.7949	Intermediate Similarity	NPC157895
0.7949	Intermediate Similarity	NPC104120
0.7949	Intermediate Similarity	NPC234193
0.7949	Intermediate Similarity	NPC236707
0.7949	Intermediate Similarity	NPC95124
0.7945	Intermediate Similarity	NPC145498
0.7941	Intermediate Similarity	NPC240506
0.7922	Intermediate Similarity	NPC474989
0.7922	Intermediate Similarity	NPC275910
0.7922	Intermediate Similarity	NPC470396
0.7922	Intermediate Similarity	NPC22955
0.7922	Intermediate Similarity	NPC297996
0.7922	Intermediate Similarity	NPC99168
0.7922	Intermediate Similarity	NPC474216
0.7917	Intermediate Similarity	NPC245795
0.7895	Intermediate Similarity	NPC1973
0.7895	Intermediate Similarity	NPC274079
0.7895	Intermediate Similarity	NPC477925
0.7895	Intermediate Similarity	NPC167873
0.7887	Intermediate Similarity	NPC475897
0.7887	Intermediate Similarity	NPC473929
0.7887	Intermediate Similarity	NPC267027
0.7875	Intermediate Similarity	NPC79945
0.7875	Intermediate Similarity	NPC317458
0.7867	Intermediate Similarity	NPC100334
0.7867	Intermediate Similarity	NPC471797
0.7867	Intermediate Similarity	NPC469534
0.7867	Intermediate Similarity	NPC469593
0.7867	Intermediate Similarity	NPC309178
0.7867	Intermediate Similarity	NPC469533
0.7857	Intermediate Similarity	NPC107540
0.7857	Intermediate Similarity	NPC101128
0.7848	Intermediate Similarity	NPC209620
0.7848	Intermediate Similarity	NPC23852
0.7848	Intermediate Similarity	NPC264245
0.7838	Intermediate Similarity	NPC469343
0.7838	Intermediate Similarity	NPC110799
0.7821	Intermediate Similarity	NPC53744
0.7821	Intermediate Similarity	NPC470429
0.7821	Intermediate Similarity	NPC308038
0.7821	Intermediate Similarity	NPC291379
0.7821	Intermediate Similarity	NPC472463
0.7805	Intermediate Similarity	NPC6391
0.7805	Intermediate Similarity	NPC473226
0.7805	Intermediate Similarity	NPC261266
0.7794	Intermediate Similarity	NPC122239
0.7792	Intermediate Similarity	NPC283619
0.7792	Intermediate Similarity	NPC101475
0.7792	Intermediate Similarity	NPC203403
0.7792	Intermediate Similarity	NPC477427
0.7792	Intermediate Similarity	NPC31037
0.7792	Intermediate Similarity	NPC474826
0.7792	Intermediate Similarity	NPC34177
0.7792	Intermediate Similarity	NPC477425
0.7792	Intermediate Similarity	NPC74995
0.7792	Intermediate Similarity	NPC214570
0.7792	Intermediate Similarity	NPC40394
0.7792	Intermediate Similarity	NPC470428
0.7792	Intermediate Similarity	NPC157996
0.7792	Intermediate Similarity	NPC477426
0.7778	Intermediate Similarity	NPC238485
0.7778	Intermediate Similarity	NPC477791
0.7778	Intermediate Similarity	NPC269077
0.7778	Intermediate Similarity	NPC253303
0.7778	Intermediate Similarity	NPC205845
0.7778	Intermediate Similarity	NPC185568
0.7778	Intermediate Similarity	NPC231310
0.7778	Intermediate Similarity	NPC139207
0.7778	Intermediate Similarity	NPC185874
0.775	Intermediate Similarity	NPC50964
0.775	Intermediate Similarity	NPC259858
0.775	Intermediate Similarity	NPC2524
0.775	Intermediate Similarity	NPC93590
0.775	Intermediate Similarity	NPC189972
0.775	Intermediate Similarity	NPC471408
0.775	Intermediate Similarity	NPC109938
0.775	Intermediate Similarity	NPC122945
0.775	Intermediate Similarity	NPC304285
0.775	Intermediate Similarity	NPC470049
0.7738	Intermediate Similarity	NPC115607
0.7733	Intermediate Similarity	NPC234527
0.7733	Intermediate Similarity	NPC14352
0.7722	Intermediate Similarity	NPC474592
0.7722	Intermediate Similarity	NPC287749
0.7722	Intermediate Similarity	NPC306095
0.7722	Intermediate Similarity	NPC164840
0.7722	Intermediate Similarity	NPC241290
0.7722	Intermediate Similarity	NPC113024
0.7722	Intermediate Similarity	NPC209944
0.7714	Intermediate Similarity	NPC473759
0.7714	Intermediate Similarity	NPC473508
0.7714	Intermediate Similarity	NPC474155
0.7703	Intermediate Similarity	NPC283316
0.7703	Intermediate Similarity	NPC189745
0.7692	Intermediate Similarity	NPC6978
0.7692	Intermediate Similarity	NPC253807

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 NPC477792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1932
0.2-0.3	4001
0.3-0.4	2133
0.4-0.5	607
0.5-0.6	251
0.6-0.7	62
0.7-0.8	13
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
0.8	Intermediate Similarity	NPD8264	Approved
0.7662	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7645	Phase 2
0.7571	Intermediate Similarity	NPD368	Approved
0.7532	Intermediate Similarity	NPD6942	Approved
0.7532	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7403	Intermediate Similarity	NPD6924	Approved
0.7403	Intermediate Similarity	NPD6926	Approved
0.7375	Intermediate Similarity	NPD6929	Approved
0.7294	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6930	Phase 2
0.7284	Intermediate Similarity	NPD6931	Approved
0.725	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6933	Approved
0.7206	Intermediate Similarity	NPD342	Phase 1
0.7143	Intermediate Similarity	NPD7152	Approved
0.7143	Intermediate Similarity	NPD7151	Approved
0.7143	Intermediate Similarity	NPD7150	Approved
0.7125	Intermediate Similarity	NPD6925	Approved
0.7125	Intermediate Similarity	NPD5776	Phase 2
0.7108	Intermediate Similarity	NPD3667	Approved
0.7105	Intermediate Similarity	NPD6922	Approved
0.7105	Intermediate Similarity	NPD6923	Approved
0.7073	Intermediate Similarity	NPD7514	Phase 3
0.7073	Intermediate Similarity	NPD7509	Discontinued
0.7073	Intermediate Similarity	NPD7332	Phase 2
0.7037	Intermediate Similarity	NPD7145	Approved
0.7024	Intermediate Similarity	NPD6695	Phase 3
0.7013	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD7143	Approved
0.6988	Remote Similarity	NPD6902	Approved
0.6977	Remote Similarity	NPD3618	Phase 1
0.6941	Remote Similarity	NPD4786	Approved
0.6941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4225	Approved
0.6867	Remote Similarity	NPD4748	Discontinued
0.686	Remote Similarity	NPD6893	Approved
0.6786	Remote Similarity	NPD6898	Phase 1
0.6742	Remote Similarity	NPD5328	Approved
0.6707	Remote Similarity	NPD6932	Approved
0.6705	Remote Similarity	NPD7524	Approved
0.6705	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD1696	Phase 3
0.6632	Remote Similarity	NPD7639	Approved
0.6632	Remote Similarity	NPD7640	Approved
0.6625	Remote Similarity	NPD4732	Discontinued
0.662	Remote Similarity	NPD4219	Approved
0.6593	Remote Similarity	NPD7515	Phase 2
0.6593	Remote Similarity	NPD6079	Approved
0.6552	Remote Similarity	NPD3666	Approved
0.6552	Remote Similarity	NPD3665	Phase 1
0.6552	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD6683	Phase 2
0.6543	Remote Similarity	NPD4784	Approved
0.6543	Remote Similarity	NPD4785	Approved
0.6526	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD4243	Approved
0.6413	Remote Similarity	NPD7087	Discontinued
0.6404	Remote Similarity	NPD5279	Phase 3
0.6364	Remote Similarity	NPD3668	Phase 3
0.6327	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD5221	Approved
0.6316	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4695	Discontinued
0.6277	Remote Similarity	NPD7748	Approved
0.6269	Remote Similarity	NPD385	Approved
0.6269	Remote Similarity	NPD384	Approved
0.6265	Remote Similarity	NPD4190	Phase 3
0.6265	Remote Similarity	NPD5275	Approved
0.625	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD4755	Approved
0.6237	Remote Similarity	NPD7637	Suspended
0.6235	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5344	Discontinued
0.6222	Remote Similarity	NPD4519	Discontinued
0.6222	Remote Similarity	NPD4623	Approved
0.62	Remote Similarity	NPD5141	Approved
0.6186	Remote Similarity	NPD5290	Discontinued
0.617	Remote Similarity	NPD6399	Phase 3
0.617	Remote Similarity	NPD5779	Approved
0.617	Remote Similarity	NPD5778	Approved
0.6163	Remote Similarity	NPD4195	Approved
0.6129	Remote Similarity	NPD7136	Phase 2
0.6122	Remote Similarity	NPD4696	Approved
0.6122	Remote Similarity	NPD5286	Approved
0.6122	Remote Similarity	NPD5285	Approved
0.6122	Remote Similarity	NPD4700	Approved
0.6092	Remote Similarity	NPD4820	Approved
0.6092	Remote Similarity	NPD4822	Approved
0.6092	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4819	Approved
0.6092	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD7902	Approved
0.6067	Remote Similarity	NPD5331	Approved
0.6067	Remote Similarity	NPD5332	Approved
0.6067	Remote Similarity	NPD5362	Discontinued
0.6064	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD4159	Approved
0.6061	Remote Similarity	NPD5223	Approved
0.6049	Remote Similarity	NPD1082	Approved
0.6047	Remote Similarity	NPD4268	Approved
0.6047	Remote Similarity	NPD4271	Approved
0.6023	Remote Similarity	NPD4790	Discontinued
0.6022	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.596	Remote Similarity	NPD6648	Approved
0.5957	Remote Similarity	NPD3168	Discontinued
0.5955	Remote Similarity	NPD4269	Approved
0.5955	Remote Similarity	NPD4221	Approved
0.5955	Remote Similarity	NPD4223	Phase 3
0.5955	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4270	Approved
0.5941	Remote Similarity	NPD4754	Approved
0.5941	Remote Similarity	NPD5175	Approved
0.5941	Remote Similarity	NPD5174	Approved
0.5934	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7154	Phase 3
0.5882	Remote Similarity	NPD4265	Approved
0.5872	Remote Similarity	NPD7115	Discovery
0.587	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6051	Approved
0.5851	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD4768	Approved
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD4767	Approved
0.5825	Remote Similarity	NPD6675	Approved
0.5824	Remote Similarity	NPD4197	Approved
0.5814	Remote Similarity	NPD1346	Approved
0.5789	Remote Similarity	NPD5785	Approved
0.5773	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7900	Approved
0.5769	Remote Similarity	NPD4194	Approved
0.5769	Remote Similarity	NPD4193	Approved
0.5769	Remote Similarity	NPD5697	Approved
0.5769	Remote Similarity	NPD4191	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5769	Remote Similarity	NPD4192	Approved
0.5761	Remote Similarity	NPD5329	Approved
0.5761	Remote Similarity	NPD5363	Approved
0.573	Remote Similarity	NPD4252	Approved
0.5729	Remote Similarity	NPD8035	Phase 2
0.5729	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD4788	Approved
0.5714	Remote Similarity	NPD5168	Approved
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD4730	Approved
0.5699	Remote Similarity	NPD4694	Approved
0.5699	Remote Similarity	NPD5330	Approved
0.5699	Remote Similarity	NPD5786	Approved
0.5699	Remote Similarity	NPD4693	Phase 3
0.5699	Remote Similarity	NPD7146	Approved
0.5699	Remote Similarity	NPD5280	Approved
0.5699	Remote Similarity	NPD7521	Approved
0.5699	Remote Similarity	NPD5690	Phase 2
0.5699	Remote Similarity	NPD4690	Approved
0.5699	Remote Similarity	NPD6409	Approved
0.5699	Remote Similarity	NPD6684	Approved
0.5699	Remote Similarity	NPD7334	Approved
0.5699	Remote Similarity	NPD4689	Approved
0.5699	Remote Similarity	NPD4138	Approved
0.5699	Remote Similarity	NPD5205	Approved
0.5699	Remote Similarity	NPD4688	Approved
0.5682	Remote Similarity	NPD3617	Approved
0.5673	Remote Similarity	NPD6640	Phase 3
0.5663	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD15	Approved
0.5663	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD791	Approved
0.566	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD6372	Approved
0.566	Remote Similarity	NPD6013	Approved
0.566	Remote Similarity	NPD6373	Approved
0.566	Remote Similarity	NPD6012	Approved
0.5641	Remote Similarity	NPD1145	Discontinued
0.5638	Remote Similarity	NPD3573	Approved
0.5634	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5700	Clinical (unspecified phase)

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