NPASS Compound

Structure

NPC145498 OpenBabel07101718242D 21 23 0 0 1 0 0 0 0 0999 V2000 3.8228 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3914 0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 1 0 0 0 17 20 1 1 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	5.351
LogD:	4.216
LogS:	-5.885
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	4.635
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.656
MDCK Permeability:	1.8574231944512576e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	94.30999755859375%
Volume Distribution (VD):	1.305
Pgp-substrate:	5.969484329223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.402
CYP2C19-inhibitor:	0.263
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.375
CYP2D6-inhibitor:	0.153
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.509

ADMET: Excretion

Clearance (CL):	2.36
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.251
Carcinogencity:	0.464
Eye Corrosion:	0.768
Eye Irritation:	0.679
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC145498

Natural Product ID:	NPC145498
*Common Name:**	Isopimara-8(14),15-Dien-11Alpha-Ol
IUPAC Name:	(2R,4R,4aS,4bS,8aS)-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-ol
Synonyms:
Standard InCHIKey:	XRBKENSBHAHCBU-DSJDWBEOSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-6-19(4)12-14-8-9-16-18(2,3)10-7-11-20(16,5)17(14)15(21)13-19/h6,12,15-17,21H,1,7-11,13H2,2-5H3/t15-,16+,17-,19-,20+/m1/s1
SMILES:	C=C[C@@]1(C)C[C@@H](O)[C@H]2C(=C1)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385636
PubChem CID:	42631361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]

☑ 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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[496832]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[496832]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[496832]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[496832]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[496832]

☑ 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 NPC145498 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	176
0.1-0.2	1340
0.2-0.3	7142
0.3-0.4	16127
0.4-0.5	8035
0.5-0.6	5893
0.6-0.7	2959
0.7-0.8	786
0.8-0.85	144
0.85-0.9	69
0.9-0.95	20
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC242001
0.9559	High Similarity	NPC243342
0.9559	High Similarity	NPC477138
0.942	High Similarity	NPC291503
0.9412	High Similarity	NPC471799
0.9412	High Similarity	NPC182717
0.9275	High Similarity	NPC471797
0.9275	High Similarity	NPC91858
0.9242	High Similarity	NPC197805
0.9155	High Similarity	NPC471798
0.9155	High Similarity	NPC91594
0.9143	High Similarity	NPC66566
0.9143	High Similarity	NPC477923
0.9104	High Similarity	NPC208999
0.9091	High Similarity	NPC222366
0.9091	High Similarity	NPC286669
0.9091	High Similarity	NPC476039
0.9014	High Similarity	NPC129165
0.9014	High Similarity	NPC113733
0.9014	High Similarity	NPC274079
0.9014	High Similarity	NPC134330
0.9014	High Similarity	NPC477925
0.9	High Similarity	NPC100334
0.8986	High Similarity	NPC110799
0.8904	High Similarity	NPC100906
0.8889	High Similarity	NPC477924
0.8873	High Similarity	NPC141071
0.8873	High Similarity	NPC22105
0.8873	High Similarity	NPC136188
0.8873	High Similarity	NPC471723
0.8873	High Similarity	NPC285893
0.8873	High Similarity	NPC134847
0.8873	High Similarity	NPC288035
0.8873	High Similarity	NPC257347
0.8873	High Similarity	NPC28657
0.8873	High Similarity	NPC304309
0.8873	High Similarity	NPC162742
0.8873	High Similarity	NPC230301
0.8857	High Similarity	NPC68443
0.8824	High Similarity	NPC32055
0.8806	High Similarity	NPC149680
0.8788	High Similarity	NPC290367
0.8788	High Similarity	NPC225415
0.8784	High Similarity	NPC287749
0.8784	High Similarity	NPC96362
0.8767	High Similarity	NPC474989
0.8767	High Similarity	NPC476314
0.8767	High Similarity	NPC22955
0.8767	High Similarity	NPC470396
0.8767	High Similarity	NPC307965
0.8767	High Similarity	NPC76931
0.8767	High Similarity	NPC99168
0.8767	High Similarity	NPC167891
0.8767	High Similarity	NPC18603
0.8767	High Similarity	NPC83351
0.875	High Similarity	NPC240604
0.875	High Similarity	NPC470362
0.875	High Similarity	NPC265328
0.875	High Similarity	NPC106432
0.875	High Similarity	NPC290598
0.875	High Similarity	NPC120098
0.875	High Similarity	NPC189883
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC30590
0.875	High Similarity	NPC253190
0.875	High Similarity	NPC27765
0.875	High Similarity	NPC265588
0.875	High Similarity	NPC300324
0.875	High Similarity	NPC321016
0.875	High Similarity	NPC106364
0.875	High Similarity	NPC107059
0.875	High Similarity	NPC122418
0.8732	High Similarity	NPC469593
0.8732	High Similarity	NPC469533
0.8732	High Similarity	NPC469534
0.8714	High Similarity	NPC167706
0.8667	High Similarity	NPC476646
0.8667	High Similarity	NPC142163
0.8657	High Similarity	NPC163678
0.8649	High Similarity	NPC291379
0.8649	High Similarity	NPC53744
0.863	High Similarity	NPC101475
0.863	High Similarity	NPC34019
0.863	High Similarity	NPC157996
0.863	High Similarity	NPC155986
0.863	High Similarity	NPC90979
0.863	High Similarity	NPC198968
0.863	High Similarity	NPC34177
0.863	High Similarity	NPC130136
0.863	High Similarity	NPC40394
0.863	High Similarity	NPC318495
0.863	High Similarity	NPC472805
0.8611	High Similarity	NPC34700
0.8611	High Similarity	NPC138374
0.8571	High Similarity	NPC92801
0.8571	High Similarity	NPC34834
0.8551	High Similarity	NPC216460
0.8533	High Similarity	NPC164840
0.8533	High Similarity	NPC241290
0.8533	High Similarity	NPC209944
0.8533	High Similarity	NPC234193
0.8514	High Similarity	NPC98386
0.8514	High Similarity	NPC477522
0.8514	High Similarity	NPC300499
0.8514	High Similarity	NPC196753
0.8514	High Similarity	NPC473943
0.8514	High Similarity	NPC275910
0.8514	High Similarity	NPC474216
0.8514	High Similarity	NPC158662
0.8514	High Similarity	NPC87604
0.8514	High Similarity	NPC253807
0.8514	High Similarity	NPC230295
0.8493	Intermediate Similarity	NPC237460
0.8493	Intermediate Similarity	NPC244488
0.8493	Intermediate Similarity	NPC96319
0.8493	Intermediate Similarity	NPC46160
0.8493	Intermediate Similarity	NPC247325
0.8493	Intermediate Similarity	NPC202642
0.8472	Intermediate Similarity	NPC306727
0.8442	Intermediate Similarity	NPC82538
0.8442	Intermediate Similarity	NPC237795
0.8429	Intermediate Similarity	NPC9942
0.8421	Intermediate Similarity	NPC474531
0.8421	Intermediate Similarity	NPC264245
0.8421	Intermediate Similarity	NPC249423
0.8421	Intermediate Similarity	NPC47761
0.8406	Intermediate Similarity	NPC69649
0.8406	Intermediate Similarity	NPC114651
0.8406	Intermediate Similarity	NPC68703
0.84	Intermediate Similarity	NPC47982
0.84	Intermediate Similarity	NPC143182
0.84	Intermediate Similarity	NPC84694
0.84	Intermediate Similarity	NPC1319
0.84	Intermediate Similarity	NPC30986
0.84	Intermediate Similarity	NPC328714
0.84	Intermediate Similarity	NPC28862
0.84	Intermediate Similarity	NPC109546
0.84	Intermediate Similarity	NPC472463
0.84	Intermediate Similarity	NPC81306
0.84	Intermediate Similarity	NPC209430
0.8378	Intermediate Similarity	NPC470711
0.8378	Intermediate Similarity	NPC470758
0.8378	Intermediate Similarity	NPC214570
0.8356	Intermediate Similarity	NPC471468
0.8356	Intermediate Similarity	NPC322353
0.8356	Intermediate Similarity	NPC121744
0.8356	Intermediate Similarity	NPC118508
0.8333	Intermediate Similarity	NPC474140
0.8312	Intermediate Similarity	NPC49964
0.8312	Intermediate Similarity	NPC248886
0.8312	Intermediate Similarity	NPC50964
0.831	Intermediate Similarity	NPC475728
0.831	Intermediate Similarity	NPC49422
0.831	Intermediate Similarity	NPC9161
0.8289	Intermediate Similarity	NPC26117
0.8289	Intermediate Similarity	NPC295131
0.8289	Intermediate Similarity	NPC236112
0.8286	Intermediate Similarity	NPC160209
0.8286	Intermediate Similarity	NPC96484
0.8286	Intermediate Similarity	NPC94192
0.8267	Intermediate Similarity	NPC72507
0.8267	Intermediate Similarity	NPC312328
0.8267	Intermediate Similarity	NPC318136
0.8267	Intermediate Similarity	NPC205455
0.8267	Intermediate Similarity	NPC11908
0.8267	Intermediate Similarity	NPC148977
0.8267	Intermediate Similarity	NPC6978
0.8267	Intermediate Similarity	NPC65897
0.8267	Intermediate Similarity	NPC477514
0.8267	Intermediate Similarity	NPC138621
0.8267	Intermediate Similarity	NPC244385
0.8267	Intermediate Similarity	NPC167037
0.8267	Intermediate Similarity	NPC85346
0.8267	Intermediate Similarity	NPC186191
0.8267	Intermediate Similarity	NPC302041
0.8267	Intermediate Similarity	NPC285761
0.8261	Intermediate Similarity	NPC476406
0.8261	Intermediate Similarity	NPC202017
0.8261	Intermediate Similarity	NPC279434
0.8243	Intermediate Similarity	NPC73875
0.8243	Intermediate Similarity	NPC470749
0.8235	Intermediate Similarity	NPC144650
0.8219	Intermediate Similarity	NPC329090
0.8219	Intermediate Similarity	NPC27395
0.8219	Intermediate Similarity	NPC201048
0.8219	Intermediate Similarity	NPC476366
0.8205	Intermediate Similarity	NPC317458
0.8205	Intermediate Similarity	NPC470384
0.8194	Intermediate Similarity	NPC164022
0.8182	Intermediate Similarity	NPC14151
0.8182	Intermediate Similarity	NPC474752
0.8182	Intermediate Similarity	NPC209620
0.8182	Intermediate Similarity	NPC474731
0.8182	Intermediate Similarity	NPC23852
0.8182	Intermediate Similarity	NPC474683
0.8182	Intermediate Similarity	NPC474759
0.8182	Intermediate Similarity	NPC242350
0.8182	Intermediate Similarity	NPC470383
0.8182	Intermediate Similarity	NPC82986
0.8182	Intermediate Similarity	NPC7505

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 NPC145498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1618
0.2-0.3	4196
0.3-0.4	2197
0.4-0.5	571
0.5-0.6	221
0.6-0.7	123
0.7-0.8	37
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8873	High Similarity	NPD7339	Approved
0.8873	High Similarity	NPD6942	Approved
0.8493	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7645	Phase 2
0.831	Intermediate Similarity	NPD7144	Approved
0.831	Intermediate Similarity	NPD7143	Approved
0.8219	Intermediate Similarity	NPD4784	Approved
0.8219	Intermediate Similarity	NPD6924	Approved
0.8219	Intermediate Similarity	NPD4785	Approved
0.8219	Intermediate Similarity	NPD6926	Approved
0.8194	Intermediate Similarity	NPD7150	Approved
0.8194	Intermediate Similarity	NPD7152	Approved
0.8194	Intermediate Similarity	NPD7151	Approved
0.8169	Intermediate Similarity	NPD6922	Approved
0.8169	Intermediate Similarity	NPD6923	Approved
0.8108	Intermediate Similarity	NPD8264	Approved
0.8052	Intermediate Similarity	NPD7525	Registered
0.8	Intermediate Similarity	NPD6933	Approved
0.7945	Intermediate Similarity	NPD4243	Approved
0.7875	Intermediate Similarity	NPD4786	Approved
0.7848	Intermediate Similarity	NPD3667	Approved
0.7821	Intermediate Similarity	NPD7509	Discontinued
0.7692	Intermediate Similarity	NPD6929	Approved
0.7662	Intermediate Similarity	NPD6932	Approved
0.7595	Intermediate Similarity	NPD6931	Approved
0.7595	Intermediate Similarity	NPD6930	Phase 2
0.7564	Intermediate Similarity	NPD7145	Approved
0.7564	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3618	Phase 1
0.7442	Intermediate Similarity	NPD6079	Approved
0.7439	Intermediate Similarity	NPD3665	Phase 1
0.7439	Intermediate Similarity	NPD3666	Approved
0.7439	Intermediate Similarity	NPD3133	Approved
0.7436	Intermediate Similarity	NPD6925	Approved
0.7436	Intermediate Similarity	NPD5776	Phase 2
0.7412	Intermediate Similarity	NPD5328	Approved
0.7403	Intermediate Similarity	NPD5275	Approved
0.7403	Intermediate Similarity	NPD4190	Phase 3
0.7381	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7514	Phase 3
0.7375	Intermediate Similarity	NPD4748	Discontinued
0.7375	Intermediate Similarity	NPD7332	Phase 2
0.7317	Intermediate Similarity	NPD6695	Phase 3
0.7284	Intermediate Similarity	NPD6902	Approved
0.725	Intermediate Similarity	NPD4195	Approved
0.725	Intermediate Similarity	NPD6683	Phase 2
0.7241	Intermediate Similarity	NPD7515	Phase 2
0.7229	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD6893	Approved
0.7073	Intermediate Similarity	NPD6898	Phase 1
0.7059	Intermediate Similarity	NPD5279	Phase 3
0.7045	Intermediate Similarity	NPD6411	Approved
0.7024	Intermediate Similarity	NPD3668	Phase 3
0.6977	Remote Similarity	NPD7750	Discontinued
0.6977	Remote Similarity	NPD7524	Approved
0.6966	Remote Similarity	NPD4202	Approved
0.6966	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5222	Approved
0.6889	Remote Similarity	NPD7748	Approved
0.6848	Remote Similarity	NPD5173	Approved
0.6818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6101	Approved
0.6818	Remote Similarity	NPD4753	Phase 2
0.6812	Remote Similarity	NPD342	Phase 1
0.6786	Remote Similarity	NPD4223	Phase 3
0.6786	Remote Similarity	NPD4221	Approved
0.6774	Remote Similarity	NPD5290	Discontinued
0.6747	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5329	Approved
0.6744	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4697	Phase 3
0.6714	Remote Similarity	NPD4219	Approved
0.6712	Remote Similarity	NPD368	Approved
0.6702	Remote Similarity	NPD5286	Approved
0.6702	Remote Similarity	NPD5285	Approved
0.6702	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6632	Remote Similarity	NPD5223	Approved
0.663	Remote Similarity	NPD4629	Approved
0.663	Remote Similarity	NPD5210	Approved
0.6628	Remote Similarity	NPD4197	Approved
0.6596	Remote Similarity	NPD7638	Approved
0.6562	Remote Similarity	NPD5211	Phase 2
0.6562	Remote Similarity	NPD5224	Approved
0.6562	Remote Similarity	NPD4633	Approved
0.6562	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD5226	Approved
0.6556	Remote Similarity	NPD7136	Phase 2
0.6526	Remote Similarity	NPD7640	Approved
0.6526	Remote Similarity	NPD7639	Approved
0.6526	Remote Similarity	NPD4700	Approved
0.6517	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6903	Approved
0.6512	Remote Similarity	NPD4788	Approved
0.6506	Remote Similarity	NPD3617	Approved
0.6495	Remote Similarity	NPD5174	Approved
0.6495	Remote Similarity	NPD5175	Approved
0.6489	Remote Similarity	NPD6084	Phase 2
0.6489	Remote Similarity	NPD6083	Phase 2
0.6484	Remote Similarity	NPD7637	Suspended
0.6477	Remote Similarity	NPD5205	Approved
0.6477	Remote Similarity	NPD4138	Approved
0.6477	Remote Similarity	NPD4690	Approved
0.6477	Remote Similarity	NPD4688	Approved
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4693	Phase 3
0.6477	Remote Similarity	NPD4689	Approved
0.6477	Remote Similarity	NPD5690	Phase 2
0.6444	Remote Similarity	NPD6051	Approved
0.6444	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5141	Approved
0.6421	Remote Similarity	NPD4225	Approved
0.6413	Remote Similarity	NPD5778	Approved
0.6413	Remote Similarity	NPD5779	Approved
0.64	Remote Similarity	NPD6881	Approved
0.64	Remote Similarity	NPD6899	Approved
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6344	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7900	Approved
0.6333	Remote Similarity	NPD4723	Approved
0.6333	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD6672	Approved
0.6333	Remote Similarity	NPD4722	Approved
0.6329	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4754	Approved
0.63	Remote Similarity	NPD5697	Approved
0.6296	Remote Similarity	NPD4732	Discontinued
0.6292	Remote Similarity	NPD5280	Approved
0.6292	Remote Similarity	NPD4694	Approved
0.6275	Remote Similarity	NPD7102	Approved
0.6275	Remote Similarity	NPD7290	Approved
0.6275	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD4787	Phase 1
0.6238	Remote Similarity	NPD6011	Approved
0.6238	Remote Similarity	NPD4729	Approved
0.6238	Remote Similarity	NPD4730	Approved
0.6238	Remote Similarity	NPD5168	Approved
0.6238	Remote Similarity	NPD7320	Approved
0.6222	Remote Similarity	NPD3573	Approved
0.6214	Remote Similarity	NPD6649	Approved
0.6214	Remote Similarity	NPD6869	Approved
0.6214	Remote Similarity	NPD6847	Approved
0.6214	Remote Similarity	NPD6650	Approved
0.6214	Remote Similarity	NPD6617	Approved
0.6214	Remote Similarity	NPD8130	Phase 1
0.6203	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4767	Approved
0.62	Remote Similarity	NPD4768	Approved
0.6176	Remote Similarity	NPD6013	Approved
0.6176	Remote Similarity	NPD6373	Approved
0.6176	Remote Similarity	NPD6012	Approved
0.6176	Remote Similarity	NPD6014	Approved
0.6176	Remote Similarity	NPD6372	Approved
0.6173	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD4518	Approved
0.6154	Remote Similarity	NPD6882	Approved
0.6139	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD6412	Phase 2
0.6129	Remote Similarity	NPD8035	Phase 2
0.6129	Remote Similarity	NPD5284	Approved
0.6129	Remote Similarity	NPD5281	Approved
0.6129	Remote Similarity	NPD8034	Phase 2
0.6125	Remote Similarity	NPD4137	Phase 3
0.6125	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4159	Approved
0.6119	Remote Similarity	NPD384	Approved
0.6119	Remote Similarity	NPD385	Approved
0.6118	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5249	Phase 3
0.6117	Remote Similarity	NPD5247	Approved
0.6117	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5248	Approved
0.6117	Remote Similarity	NPD4634	Approved
0.6117	Remote Similarity	NPD5251	Approved
0.6117	Remote Similarity	NPD5250	Approved
0.6117	Remote Similarity	NPD5169	Approved
0.6117	Remote Similarity	NPD5135	Approved
0.6111	Remote Similarity	NPD6098	Approved
0.6105	Remote Similarity	NPD5695	Phase 3
0.6092	Remote Similarity	NPD4139	Approved
0.6092	Remote Similarity	NPD4692	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