NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	3.668
LogD:	3.619
LogS:	-3.265
# 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:	4.269
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:	-4.405
MDCK Permeability:	1.9058026737184264e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.606
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.375
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	93.77413177490234%
Volume Distribution (VD):	1.001
Pgp-substrate:	4.7850141525268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	10.473
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.316
Skin Sensitization:	0.374
Carcinogencity:	0.068
Eye Corrosion:	0.869
Eye Irritation:	0.965
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC92801

Natural Product ID:	NPC92801
*Common Name:**	5Alpha,10Beta-3-Eudesmen-1Beta,6Alpha-Diol
IUPAC Name:	(1S,2R,4aR,5R,8aS)-4a,8-dimethyl-2-propan-2-yl-2,3,4,5,6,8a-hexahydro-1H-naphthalene-1,5-diol
Synonyms:
Standard InCHIKey:	FQTDJSUKIPVNPW-ZSAUSMIDSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-9(2)11-7-8-15(4)12(16)6-5-10(3)13(15)14(11)17/h5,9,11-14,16-17H,6-8H2,1-4H3/t11-,12-,13-,14+,15+/m1/s1
SMILES:	CC1=CC[C@H]([C@]2([C@H]1[C@@H](O)[C@H](CC2)C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507427
PubChem CID:	44559491
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
NPO32645	croton arboreous	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165166]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	28.0	%	PMID[538921]

☑ 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 NPC92801 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	165
0.1-0.2	1415
0.2-0.3	6483
0.3-0.4	16177
0.4-0.5	8489
0.5-0.6	5933
0.6-0.7	3104
0.7-0.8	789
0.8-0.85	96
0.85-0.9	43
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC164022
0.9143	High Similarity	NPC291503
0.9104	High Similarity	NPC208999
0.9014	High Similarity	NPC265588
0.9	High Similarity	NPC477138
0.9	High Similarity	NPC243342
0.8986	High Similarity	NPC23954
0.8986	High Similarity	NPC167706
0.8986	High Similarity	NPC242992
0.8939	High Similarity	NPC60837
0.8939	High Similarity	NPC208198
0.8939	High Similarity	NPC172613
0.8939	High Similarity	NPC11555
0.8939	High Similarity	NPC2728
0.8939	High Similarity	NPC282619
0.8889	High Similarity	NPC471798
0.8873	High Similarity	NPC66566
0.8873	High Similarity	NPC477923
0.8857	High Similarity	NPC220939
0.8857	High Similarity	NPC265485
0.8857	High Similarity	NPC471799
0.8857	High Similarity	NPC182717
0.8824	High Similarity	NPC96484
0.8788	High Similarity	NPC144650
0.8767	High Similarity	NPC300499
0.8767	High Similarity	NPC474989
0.8767	High Similarity	NPC470396
0.8767	High Similarity	NPC275910
0.8767	High Similarity	NPC22955
0.8767	High Similarity	NPC99168
0.875	High Similarity	NPC274079
0.875	High Similarity	NPC106432
0.875	High Similarity	NPC477925
0.8732	High Similarity	NPC100334
0.8732	High Similarity	NPC91858
0.8732	High Similarity	NPC471797
0.8714	High Similarity	NPC242001
0.8714	High Similarity	NPC477792
0.8714	High Similarity	NPC110799
0.8676	High Similarity	NPC139207
0.8676	High Similarity	NPC185874
0.8667	High Similarity	NPC476646
0.8649	High Similarity	NPC291379
0.8649	High Similarity	NPC53744
0.863	High Similarity	NPC101475
0.863	High Similarity	NPC40394
0.863	High Similarity	NPC214570
0.863	High Similarity	NPC157996
0.863	High Similarity	NPC477924
0.863	High Similarity	NPC91594
0.863	High Similarity	NPC34177
0.863	High Similarity	NPC130136
0.863	High Similarity	NPC90979
0.863	High Similarity	NPC472805
0.8592	High Similarity	NPC474140
0.8592	High Similarity	NPC68443
0.8571	High Similarity	NPC34834
0.8571	High Similarity	NPC145498
0.8551	High Similarity	NPC471238
0.8533	High Similarity	NPC96362
0.8533	High Similarity	NPC287749
0.8529	High Similarity	NPC473929
0.8529	High Similarity	NPC202017
0.8514	High Similarity	NPC98386
0.8514	High Similarity	NPC244385
0.8514	High Similarity	NPC196753
0.8514	High Similarity	NPC6978
0.8514	High Similarity	NPC230295
0.8514	High Similarity	NPC167037
0.8514	High Similarity	NPC158662
0.8514	High Similarity	NPC138621
0.8514	High Similarity	NPC253807
0.8507	High Similarity	NPC290367
0.8507	High Similarity	NPC101128
0.8507	High Similarity	NPC225415
0.8493	Intermediate Similarity	NPC300324
0.8493	Intermediate Similarity	NPC265328
0.8493	Intermediate Similarity	NPC96319
0.8493	Intermediate Similarity	NPC120098
0.8493	Intermediate Similarity	NPC290598
0.8493	Intermediate Similarity	NPC240604
0.8493	Intermediate Similarity	NPC46160
0.8493	Intermediate Similarity	NPC106364
0.8493	Intermediate Similarity	NPC122418
0.8493	Intermediate Similarity	NPC202642
0.8493	Intermediate Similarity	NPC30590
0.8493	Intermediate Similarity	NPC321381
0.8493	Intermediate Similarity	NPC27765
0.8493	Intermediate Similarity	NPC73875
0.8493	Intermediate Similarity	NPC321016
0.8493	Intermediate Similarity	NPC107059
0.8493	Intermediate Similarity	NPC189883
0.8485	Intermediate Similarity	NPC282694
0.8485	Intermediate Similarity	NPC79576
0.8485	Intermediate Similarity	NPC194208
0.8472	Intermediate Similarity	NPC476366
0.8472	Intermediate Similarity	NPC201048
0.8451	Intermediate Similarity	NPC471272
0.8429	Intermediate Similarity	NPC474248
0.8421	Intermediate Similarity	NPC474531
0.8421	Intermediate Similarity	NPC473420
0.8406	Intermediate Similarity	NPC253303
0.8406	Intermediate Similarity	NPC269077
0.84	Intermediate Similarity	NPC470429
0.84	Intermediate Similarity	NPC1319
0.84	Intermediate Similarity	NPC80530
0.84	Intermediate Similarity	NPC273410
0.84	Intermediate Similarity	NPC472463
0.8378	Intermediate Similarity	NPC318495
0.8378	Intermediate Similarity	NPC155986
0.8378	Intermediate Similarity	NPC470711
0.8378	Intermediate Similarity	NPC283619
0.8378	Intermediate Similarity	NPC198968
0.8378	Intermediate Similarity	NPC470758
0.8356	Intermediate Similarity	NPC257347
0.8356	Intermediate Similarity	NPC230301
0.8356	Intermediate Similarity	NPC304309
0.8356	Intermediate Similarity	NPC121744
0.8356	Intermediate Similarity	NPC288035
0.8356	Intermediate Similarity	NPC34700
0.8356	Intermediate Similarity	NPC162742
0.8356	Intermediate Similarity	NPC138374
0.8356	Intermediate Similarity	NPC22105
0.8356	Intermediate Similarity	NPC136188
0.8356	Intermediate Similarity	NPC134847
0.8356	Intermediate Similarity	NPC285893
0.8356	Intermediate Similarity	NPC141071
0.8356	Intermediate Similarity	NPC322353
0.8356	Intermediate Similarity	NPC118508
0.8356	Intermediate Similarity	NPC28657
0.8356	Intermediate Similarity	NPC471723
0.8333	Intermediate Similarity	NPC46320
0.8333	Intermediate Similarity	NPC95165
0.8333	Intermediate Similarity	NPC124172
0.8333	Intermediate Similarity	NPC238992
0.8312	Intermediate Similarity	NPC248886
0.8312	Intermediate Similarity	NPC201852
0.8289	Intermediate Similarity	NPC102253
0.8289	Intermediate Similarity	NPC295131
0.8289	Intermediate Similarity	NPC236237
0.8289	Intermediate Similarity	NPC236112
0.8289	Intermediate Similarity	NPC322313
0.8286	Intermediate Similarity	NPC276616
0.8286	Intermediate Similarity	NPC244790
0.8267	Intermediate Similarity	NPC167891
0.8267	Intermediate Similarity	NPC72507
0.8267	Intermediate Similarity	NPC474216
0.8267	Intermediate Similarity	NPC318136
0.8267	Intermediate Similarity	NPC477522
0.8267	Intermediate Similarity	NPC87604
0.8267	Intermediate Similarity	NPC205455
0.8267	Intermediate Similarity	NPC476314
0.8267	Intermediate Similarity	NPC473943
0.8267	Intermediate Similarity	NPC186191
0.8267	Intermediate Similarity	NPC83351
0.8267	Intermediate Similarity	NPC285761
0.8243	Intermediate Similarity	NPC167873
0.8243	Intermediate Similarity	NPC253190
0.8243	Intermediate Similarity	NPC134330
0.8243	Intermediate Similarity	NPC1973
0.8243	Intermediate Similarity	NPC113733
0.8243	Intermediate Similarity	NPC237460
0.8243	Intermediate Similarity	NPC129165
0.8243	Intermediate Similarity	NPC470362
0.8243	Intermediate Similarity	NPC470749
0.8235	Intermediate Similarity	NPC68656
0.8235	Intermediate Similarity	NPC323424
0.8235	Intermediate Similarity	NPC96793
0.8219	Intermediate Similarity	NPC306727
0.8205	Intermediate Similarity	NPC237795
0.8205	Intermediate Similarity	NPC253402
0.8205	Intermediate Similarity	NPC159168
0.8205	Intermediate Similarity	NPC82538
0.8194	Intermediate Similarity	NPC471271
0.8194	Intermediate Similarity	NPC471268
0.8182	Intermediate Similarity	NPC142163
0.8182	Intermediate Similarity	NPC242350
0.8182	Intermediate Similarity	NPC470383
0.8182	Intermediate Similarity	NPC116202
0.8169	Intermediate Similarity	NPC471560
0.8158	Intermediate Similarity	NPC81306
0.8158	Intermediate Similarity	NPC109546
0.8158	Intermediate Similarity	NPC28862
0.8158	Intermediate Similarity	NPC47982
0.8158	Intermediate Similarity	NPC209430
0.8158	Intermediate Similarity	NPC328714
0.8158	Intermediate Similarity	NPC143182
0.8158	Intermediate Similarity	NPC84694
0.8158	Intermediate Similarity	NPC30986
0.8143	Intermediate Similarity	NPC197805
0.8143	Intermediate Similarity	NPC171225
0.8143	Intermediate Similarity	NPC114651
0.8133	Intermediate Similarity	NPC34019
0.8133	Intermediate Similarity	NPC197659
0.8133	Intermediate Similarity	NPC470428
0.8125	Intermediate Similarity	NPC6979
0.8125	Intermediate Similarity	NPC473226
0.8125	Intermediate Similarity	NPC24277
0.8125	Intermediate Similarity	NPC237344
0.8116	Intermediate Similarity	NPC258595

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 NPC92801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1899
0.2-0.3	4069
0.3-0.4	2111
0.4-0.5	546
0.5-0.6	239
0.6-0.7	110
0.7-0.8	28
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
0.8493	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7645	Phase 2
0.8356	Intermediate Similarity	NPD6942	Approved
0.8356	Intermediate Similarity	NPD7339	Approved
0.8289	Intermediate Similarity	NPD7525	Registered
0.7867	Intermediate Similarity	NPD8264	Approved
0.7848	Intermediate Similarity	NPD3667	Approved
0.7733	Intermediate Similarity	NPD6924	Approved
0.7733	Intermediate Similarity	NPD6926	Approved
0.7683	Intermediate Similarity	NPD3618	Phase 1
0.7681	Intermediate Similarity	NPD368	Approved
0.7654	Intermediate Similarity	NPD4786	Approved
0.7595	Intermediate Similarity	NPD4748	Discontinued
0.7595	Intermediate Similarity	NPD7509	Discontinued
0.7532	Intermediate Similarity	NPD6933	Approved
0.7467	Intermediate Similarity	NPD7151	Approved
0.7467	Intermediate Similarity	NPD7150	Approved
0.7467	Intermediate Similarity	NPD7152	Approved
0.7432	Intermediate Similarity	NPD6923	Approved
0.7432	Intermediate Similarity	NPD6922	Approved
0.7412	Intermediate Similarity	NPD5328	Approved
0.7381	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD7143	Approved
0.7333	Intermediate Similarity	NPD7144	Approved
0.7273	Intermediate Similarity	NPD4785	Approved
0.7273	Intermediate Similarity	NPD4784	Approved
0.725	Intermediate Similarity	NPD6929	Approved
0.7241	Intermediate Similarity	NPD7515	Phase 2
0.7241	Intermediate Similarity	NPD6079	Approved
0.7237	Intermediate Similarity	NPD4243	Approved
0.7229	Intermediate Similarity	NPD3665	Phase 1
0.7229	Intermediate Similarity	NPD3133	Approved
0.7229	Intermediate Similarity	NPD3666	Approved
0.716	Intermediate Similarity	NPD6931	Approved
0.716	Intermediate Similarity	NPD6930	Phase 2
0.7059	Intermediate Similarity	NPD342	Phase 1
0.7033	Intermediate Similarity	NPD4755	Approved
0.7024	Intermediate Similarity	NPD3668	Phase 3
0.7024	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6932	Approved
0.7	Intermediate Similarity	NPD5776	Phase 2
0.7	Intermediate Similarity	NPD6925	Approved
0.6966	Remote Similarity	NPD6399	Phase 3
0.6962	Remote Similarity	NPD4190	Phase 3
0.6962	Remote Similarity	NPD5275	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD5222	Approved
0.6914	Remote Similarity	NPD7145	Approved
0.6914	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6695	Phase 3
0.6889	Remote Similarity	NPD7748	Approved
0.6882	Remote Similarity	NPD4700	Approved
0.6882	Remote Similarity	NPD4696	Approved
0.6882	Remote Similarity	NPD5286	Approved
0.6882	Remote Similarity	NPD5285	Approved
0.686	Remote Similarity	NPD5279	Phase 3
0.6848	Remote Similarity	NPD7902	Approved
0.6848	Remote Similarity	NPD5173	Approved
0.6829	Remote Similarity	NPD6683	Phase 2
0.6829	Remote Similarity	NPD4195	Approved
0.6809	Remote Similarity	NPD5223	Approved
0.6774	Remote Similarity	NPD5290	Discontinued
0.6747	Remote Similarity	NPD7332	Phase 2
0.6747	Remote Similarity	NPD7514	Phase 3
0.6747	Remote Similarity	NPD4695	Discontinued
0.6744	Remote Similarity	NPD6893	Approved
0.6744	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5211	Phase 2
0.6737	Remote Similarity	NPD5226	Approved
0.6737	Remote Similarity	NPD5224	Approved
0.6737	Remote Similarity	NPD4633	Approved
0.6737	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD6898	Phase 1
0.6667	Remote Similarity	NPD5174	Approved
0.6629	Remote Similarity	NPD4753	Phase 2
0.6615	Remote Similarity	NPD384	Approved
0.6615	Remote Similarity	NPD385	Approved
0.6598	Remote Similarity	NPD5141	Approved
0.6596	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD4225	Approved
0.6591	Remote Similarity	NPD7750	Discontinued
0.6591	Remote Similarity	NPD7524	Approved
0.6588	Remote Similarity	NPD4221	Approved
0.6588	Remote Similarity	NPD4223	Phase 3
0.6552	Remote Similarity	NPD1696	Phase 3
0.6548	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD4768	Approved
0.6531	Remote Similarity	NPD5739	Approved
0.6531	Remote Similarity	NPD7128	Approved
0.6531	Remote Similarity	NPD4767	Approved
0.6531	Remote Similarity	NPD6675	Approved
0.6526	Remote Similarity	NPD7640	Approved
0.6526	Remote Similarity	NPD7639	Approved
0.6522	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD6411	Approved
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD5701	Approved
0.6437	Remote Similarity	NPD4197	Approved
0.64	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD4730	Approved
0.64	Remote Similarity	NPD5128	Approved
0.64	Remote Similarity	NPD6881	Approved
0.64	Remote Similarity	NPD6899	Approved
0.64	Remote Similarity	NPD7320	Approved
0.6364	Remote Similarity	NPD5329	Approved
0.6337	Remote Similarity	NPD6012	Approved
0.6337	Remote Similarity	NPD6014	Approved
0.6337	Remote Similarity	NPD6373	Approved
0.6337	Remote Similarity	NPD6013	Approved
0.6337	Remote Similarity	NPD6372	Approved
0.6329	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3617	Approved
0.6304	Remote Similarity	NPD7087	Discontinued
0.6304	Remote Similarity	NPD8034	Phase 2
0.6304	Remote Similarity	NPD8035	Phase 2
0.6292	Remote Similarity	NPD4623	Approved
0.6292	Remote Similarity	NPD5690	Phase 2
0.6292	Remote Similarity	NPD5280	Approved
0.6292	Remote Similarity	NPD4689	Approved
0.6292	Remote Similarity	NPD4519	Discontinued
0.6292	Remote Similarity	NPD6409	Approved
0.6292	Remote Similarity	NPD7334	Approved
0.6292	Remote Similarity	NPD4688	Approved
0.6292	Remote Similarity	NPD6684	Approved
0.6292	Remote Similarity	NPD5205	Approved
0.6292	Remote Similarity	NPD4138	Approved
0.6292	Remote Similarity	NPD4694	Approved
0.6292	Remote Similarity	NPD5330	Approved
0.6292	Remote Similarity	NPD7146	Approved
0.6292	Remote Similarity	NPD4690	Approved
0.6292	Remote Similarity	NPD4693	Phase 3
0.6292	Remote Similarity	NPD7521	Approved
0.6289	Remote Similarity	NPD4159	Approved
0.6277	Remote Similarity	NPD5210	Approved
0.6277	Remote Similarity	NPD4629	Approved
0.6275	Remote Similarity	NPD5250	Approved
0.6275	Remote Similarity	NPD5169	Approved
0.6275	Remote Similarity	NPD5247	Approved
0.6275	Remote Similarity	NPD5251	Approved
0.6275	Remote Similarity	NPD5248	Approved
0.6275	Remote Similarity	NPD5249	Phase 3
0.6275	Remote Similarity	NPD7102	Approved
0.6275	Remote Similarity	NPD4634	Approved
0.6275	Remote Similarity	NPD5135	Approved
0.6275	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7290	Approved
0.6275	Remote Similarity	NPD6883	Approved
0.6265	Remote Similarity	NPD1346	Approved
0.6264	Remote Similarity	NPD6101	Approved
0.6264	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4219	Approved
0.6238	Remote Similarity	NPD5168	Approved
0.6222	Remote Similarity	NPD3573	Approved
0.6214	Remote Similarity	NPD6649	Approved
0.6214	Remote Similarity	NPD6869	Approved
0.6214	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5216	Approved
0.6214	Remote Similarity	NPD6847	Approved
0.6214	Remote Similarity	NPD6650	Approved
0.6214	Remote Similarity	NPD5215	Approved
0.6214	Remote Similarity	NPD6617	Approved
0.6214	Remote Similarity	NPD5217	Approved
0.6214	Remote Similarity	NPD5127	Approved
0.6214	Remote Similarity	NPD8130	Phase 1
0.6196	Remote Similarity	NPD3168	Discontinued
0.618	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD4722	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4723	Approved
0.6154	Remote Similarity	NPD6882	Approved
0.6146	Remote Similarity	NPD6084	Phase 2
0.6146	Remote Similarity	NPD6083	Phase 2
0.6136	Remote Similarity	NPD4788	Approved
0.6129	Remote Similarity	NPD5281	Approved
0.6129	Remote Similarity	NPD5284	Approved
0.6125	Remote Similarity	NPD15	Approved
0.6125	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD791	Approved
0.6105	Remote Similarity	NPD5695	Phase 3
0.6104	Remote Similarity	NPD371	Approved
0.6098	Remote Similarity	NPD4732	Discontinued
0.6095	Remote Similarity	NPD4632	Approved
0.6092	Remote Similarity	NPD4139	Approved
0.6092	Remote Similarity	NPD4692	Approved
0.6087	Remote Similarity	NPD6051	Approved
0.6087	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5778	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