NPASS Compound

Structure

NPC208999 OpenBabel07101719522D 21 22 0 0 1 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 1.7321 -0.0000 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 0.5000 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 -4.3301 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 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 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 16 18 1 0 0 0 0 17 15 1 1 0 0 0 18 20 1 1 0 0 0 19 20 1 1 0 0 0 19 21 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.925
LogD:	4.318
LogS:	-4.194
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	4.411
Fsp3:	0.7
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:	-4.57
MDCK Permeability:	1.458679798815865e-05
Pgp-inhibitor:	0.894
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	93.56697845458984%
Volume Distribution (VD):	1.85
Pgp-substrate:	5.321133136749268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.683
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.495
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	17.37
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.839
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.518
Carcinogencity:	0.236
Eye Corrosion:	0.06
Eye Irritation:	0.173
Respiratory Toxicity:	0.71

Download Data

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

Natural Product: NPC208999

Natural Product ID:	NPC208999
*Common Name:**	Gyrosanol A
IUPAC Name:	(1S,4aR,6S,8aS)-4,8a-dimethyl-6-(6-methylhepta-1,5-dien-2-yl)-2,4a,5,6,7,8-hexahydro-1H-naphthalen-1-ol
Synonyms:
Standard InCHIKey:	NJRDJVYVVKTPQA-YRPNKDGESA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14(2)7-6-8-15(3)17-11-12-20(5)18(13-17)16(4)9-10-19(20)21/h7,9,17-19,21H,3,6,8,10-13H2,1-2,4-5H3/t17-,18+,19-,20-/m0/s1
SMILES:	CC(=CCCC(=C)[C@H]1CC[C@]2([C@H](C1)C(=CC[C@@H]2O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163918
PubChem CID:	46848860
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
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	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
IC50	1
Others	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	16.9	%	PMID[469580]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	118.5	%	PMID[469580]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	2600.0	nM	PMID[469580]

☑ 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 NPC208999 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	174
0.1-0.2	1483
0.2-0.3	8627
0.3-0.4	15158
0.4-0.5	7791
0.5-0.6	5771
0.6-0.7	2852
0.7-0.8	666
0.8-0.85	135
0.85-0.9	34
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC471799
0.9365	High Similarity	NPC290367
0.9265	High Similarity	NPC471797
0.913	High Similarity	NPC136188
0.913	High Similarity	NPC162742
0.913	High Similarity	NPC288035
0.913	High Similarity	NPC22105
0.913	High Similarity	NPC285893
0.913	High Similarity	NPC304309
0.913	High Similarity	NPC230301
0.913	High Similarity	NPC28657
0.913	High Similarity	NPC134847
0.9118	High Similarity	NPC182717
0.9104	High Similarity	NPC34834
0.9104	High Similarity	NPC92801
0.9104	High Similarity	NPC145498
0.9	High Similarity	NPC107059
0.9	High Similarity	NPC106364
0.9	High Similarity	NPC240604
0.9	High Similarity	NPC321016
0.9	High Similarity	NPC300324
0.9	High Similarity	NPC321381
0.9	High Similarity	NPC265588
0.9	High Similarity	NPC113733
0.8986	High Similarity	NPC477138
0.8986	High Similarity	NPC100334
0.8986	High Similarity	NPC243342
0.8971	High Similarity	NPC167706
0.8971	High Similarity	NPC242001
0.8971	High Similarity	NPC110799
0.8939	High Similarity	NPC114651
0.8939	High Similarity	NPC197805
0.8873	High Similarity	NPC471798
0.8873	High Similarity	NPC34019
0.8873	High Similarity	NPC318495
0.8873	High Similarity	NPC155986
0.8873	High Similarity	NPC198968
0.8857	High Similarity	NPC291503
0.8857	High Similarity	NPC141071
0.8857	High Similarity	NPC66566
0.8857	High Similarity	NPC471723
0.8857	High Similarity	NPC257347
0.8857	High Similarity	NPC477923
0.8841	High Similarity	NPC474140
0.8806	High Similarity	NPC96484
0.8806	High Similarity	NPC216460
0.8788	High Similarity	NPC286669
0.8788	High Similarity	NPC202017
0.8788	High Similarity	NPC476039
0.8788	High Similarity	NPC222366
0.8769	High Similarity	NPC225415
0.875	High Similarity	NPC167891
0.875	High Similarity	NPC18603
0.875	High Similarity	NPC307965
0.875	High Similarity	NPC470396
0.875	High Similarity	NPC76931
0.875	High Similarity	NPC99168
0.875	High Similarity	NPC474216
0.875	High Similarity	NPC83351
0.875	High Similarity	NPC22955
0.875	High Similarity	NPC474989
0.875	High Similarity	NPC477522
0.875	High Similarity	NPC87604
0.875	High Similarity	NPC275910
0.875	High Similarity	NPC473943
0.8732	High Similarity	NPC290598
0.8732	High Similarity	NPC274079
0.8732	High Similarity	NPC477925
0.8732	High Similarity	NPC122418
0.8732	High Similarity	NPC96319
0.8732	High Similarity	NPC120098
0.8732	High Similarity	NPC46160
0.8732	High Similarity	NPC27765
0.8732	High Similarity	NPC189883
0.8732	High Similarity	NPC30590
0.8732	High Similarity	NPC134330
0.8732	High Similarity	NPC265328
0.8732	High Similarity	NPC129165
0.8732	High Similarity	NPC202642
0.8732	High Similarity	NPC470362
0.8714	High Similarity	NPC91858
0.8696	High Similarity	NPC164022
0.8676	High Similarity	NPC474248
0.8636	High Similarity	NPC163678
0.863	High Similarity	NPC143182
0.863	High Similarity	NPC28862
0.863	High Similarity	NPC53744
0.863	High Similarity	NPC328714
0.863	High Similarity	NPC81306
0.863	High Similarity	NPC109546
0.863	High Similarity	NPC47982
0.863	High Similarity	NPC84694
0.863	High Similarity	NPC291379
0.8611	High Similarity	NPC40394
0.8611	High Similarity	NPC472805
0.8611	High Similarity	NPC34177
0.8611	High Similarity	NPC91594
0.8611	High Similarity	NPC214570
0.8611	High Similarity	NPC157996
0.8611	High Similarity	NPC101475
0.8611	High Similarity	NPC90979
0.8611	High Similarity	NPC477924
0.8592	High Similarity	NPC118508
0.8592	High Similarity	NPC121744
0.8592	High Similarity	NPC34700
0.8592	High Similarity	NPC138374
0.8592	High Similarity	NPC322353
0.8571	High Similarity	NPC68443
0.8529	High Similarity	NPC32055
0.8529	High Similarity	NPC160209
0.8514	High Similarity	NPC234193
0.8514	High Similarity	NPC164840
0.8514	High Similarity	NPC241290
0.8514	High Similarity	NPC26117
0.8514	High Similarity	NPC209944
0.8507	High Similarity	NPC149680
0.8507	High Similarity	NPC279434
0.8493	Intermediate Similarity	NPC196753
0.8493	Intermediate Similarity	NPC318136
0.8493	Intermediate Similarity	NPC98386
0.8493	Intermediate Similarity	NPC253807
0.8493	Intermediate Similarity	NPC186191
0.8493	Intermediate Similarity	NPC230295
0.8493	Intermediate Similarity	NPC205455
0.8493	Intermediate Similarity	NPC158662
0.8493	Intermediate Similarity	NPC300499
0.8493	Intermediate Similarity	NPC476314
0.8472	Intermediate Similarity	NPC244488
0.8472	Intermediate Similarity	NPC237460
0.8472	Intermediate Similarity	NPC106432
0.8472	Intermediate Similarity	NPC73875
0.8472	Intermediate Similarity	NPC247325
0.8451	Intermediate Similarity	NPC306727
0.8451	Intermediate Similarity	NPC469534
0.8451	Intermediate Similarity	NPC469593
0.8451	Intermediate Similarity	NPC476366
0.8451	Intermediate Similarity	NPC469533
0.8451	Intermediate Similarity	NPC201048
0.8429	Intermediate Similarity	NPC242992
0.8406	Intermediate Similarity	NPC471560
0.84	Intermediate Similarity	NPC476646
0.84	Intermediate Similarity	NPC209620
0.84	Intermediate Similarity	NPC474731
0.84	Intermediate Similarity	NPC474683
0.84	Intermediate Similarity	NPC264245
0.84	Intermediate Similarity	NPC47761
0.84	Intermediate Similarity	NPC474759
0.84	Intermediate Similarity	NPC7505
0.84	Intermediate Similarity	NPC474531
0.84	Intermediate Similarity	NPC474752
0.84	Intermediate Similarity	NPC82986
0.84	Intermediate Similarity	NPC470383
0.84	Intermediate Similarity	NPC23852
0.8382	Intermediate Similarity	NPC69649
0.8382	Intermediate Similarity	NPC68703
0.8382	Intermediate Similarity	NPC171225
0.8378	Intermediate Similarity	NPC472463
0.8378	Intermediate Similarity	NPC30986
0.8378	Intermediate Similarity	NPC209430
0.8378	Intermediate Similarity	NPC1319
0.8356	Intermediate Similarity	NPC283619
0.8356	Intermediate Similarity	NPC470711
0.8356	Intermediate Similarity	NPC470758
0.8356	Intermediate Similarity	NPC130136
0.8333	Intermediate Similarity	NPC471468
0.831	Intermediate Similarity	NPC265485
0.831	Intermediate Similarity	NPC220939
0.831	Intermediate Similarity	NPC201373
0.8289	Intermediate Similarity	NPC201852
0.8289	Intermediate Similarity	NPC470614
0.8289	Intermediate Similarity	NPC1272
0.8289	Intermediate Similarity	NPC101462
0.8289	Intermediate Similarity	NPC50964
0.8289	Intermediate Similarity	NPC5985
0.8289	Intermediate Similarity	NPC49964
0.8289	Intermediate Similarity	NPC189972
0.8289	Intermediate Similarity	NPC248886
0.8267	Intermediate Similarity	NPC96362
0.8267	Intermediate Similarity	NPC295131
0.8267	Intermediate Similarity	NPC236112
0.8267	Intermediate Similarity	NPC287749
0.8261	Intermediate Similarity	NPC94192
0.8243	Intermediate Similarity	NPC72507
0.8243	Intermediate Similarity	NPC312328
0.8243	Intermediate Similarity	NPC138621
0.8243	Intermediate Similarity	NPC6978
0.8243	Intermediate Similarity	NPC167037
0.8243	Intermediate Similarity	NPC65897
0.8243	Intermediate Similarity	NPC477514
0.8243	Intermediate Similarity	NPC244385
0.8243	Intermediate Similarity	NPC85346
0.8243	Intermediate Similarity	NPC285761
0.8243	Intermediate Similarity	NPC302041
0.8235	Intermediate Similarity	NPC250977
0.8235	Intermediate Similarity	NPC473929
0.8219	Intermediate Similarity	NPC470749
0.8219	Intermediate Similarity	NPC253190
0.8209	Intermediate Similarity	NPC323424
0.8209	Intermediate Similarity	NPC144650
0.8209	Intermediate Similarity	NPC96793

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 NPC208999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1971
0.2-0.3	4127
0.3-0.4	2032
0.4-0.5	494
0.5-0.6	235
0.6-0.7	90
0.7-0.8	36
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD6942	Approved
0.913	High Similarity	NPD7339	Approved
0.8732	High Similarity	NPD3701	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD7645	Phase 2
0.8194	Intermediate Similarity	NPD6924	Approved
0.8194	Intermediate Similarity	NPD6926	Approved
0.8169	Intermediate Similarity	NPD7151	Approved
0.8169	Intermediate Similarity	NPD7150	Approved
0.8169	Intermediate Similarity	NPD7152	Approved
0.8143	Intermediate Similarity	NPD6922	Approved
0.8143	Intermediate Similarity	NPD6923	Approved
0.8082	Intermediate Similarity	NPD8264	Approved
0.8077	Intermediate Similarity	NPD4786	Approved
0.8052	Intermediate Similarity	NPD3667	Approved
0.8028	Intermediate Similarity	NPD7143	Approved
0.8028	Intermediate Similarity	NPD7144	Approved
0.8026	Intermediate Similarity	NPD7525	Registered
0.7973	Intermediate Similarity	NPD6933	Approved
0.7945	Intermediate Similarity	NPD4785	Approved
0.7945	Intermediate Similarity	NPD4784	Approved
0.7917	Intermediate Similarity	NPD4243	Approved
0.7662	Intermediate Similarity	NPD6929	Approved
0.7564	Intermediate Similarity	NPD6930	Phase 2
0.7564	Intermediate Similarity	NPD4748	Discontinued
0.7564	Intermediate Similarity	NPD7509	Discontinued
0.7564	Intermediate Similarity	NPD6931	Approved
0.7561	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3618	Phase 1
0.7407	Intermediate Similarity	NPD3133	Approved
0.7407	Intermediate Similarity	NPD3665	Phase 1
0.7407	Intermediate Similarity	NPD3666	Approved
0.7403	Intermediate Similarity	NPD6932	Approved
0.7403	Intermediate Similarity	NPD6925	Approved
0.7403	Intermediate Similarity	NPD5776	Phase 2
0.7381	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD4190	Phase 3
0.7368	Intermediate Similarity	NPD5275	Approved
0.7308	Intermediate Similarity	NPD7145	Approved
0.7308	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD342	Phase 1
0.7215	Intermediate Similarity	NPD6683	Phase 2
0.7209	Intermediate Similarity	NPD6079	Approved
0.7209	Intermediate Similarity	NPD7515	Phase 2
0.7195	Intermediate Similarity	NPD3668	Phase 3
0.7195	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD368	Approved
0.7126	Intermediate Similarity	NPD6399	Phase 3
0.7125	Intermediate Similarity	NPD7332	Phase 2
0.7125	Intermediate Similarity	NPD7514	Phase 3
0.7108	Intermediate Similarity	NPD6893	Approved
0.7037	Intermediate Similarity	NPD6898	Phase 1
0.7037	Intermediate Similarity	NPD6902	Approved
0.7024	Intermediate Similarity	NPD5279	Phase 3
0.7	Intermediate Similarity	NPD4195	Approved
0.6941	Remote Similarity	NPD7750	Discontinued
0.6941	Remote Similarity	NPD7524	Approved
0.6932	Remote Similarity	NPD4202	Approved
0.6914	Remote Similarity	NPD4695	Discontinued
0.6854	Remote Similarity	NPD7748	Approved
0.6782	Remote Similarity	NPD4753	Phase 2
0.6747	Remote Similarity	NPD4221	Approved
0.6747	Remote Similarity	NPD4223	Phase 3
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5329	Approved
0.6706	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4697	Phase 3
0.6703	Remote Similarity	NPD5222	Approved
0.6703	Remote Similarity	NPD5221	Approved
0.6703	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4219	Approved
0.663	Remote Similarity	NPD4755	Approved
0.663	Remote Similarity	NPD5173	Approved
0.663	Remote Similarity	NPD7902	Approved
0.6629	Remote Similarity	NPD6411	Approved
0.6629	Remote Similarity	NPD7087	Discontinued
0.6628	Remote Similarity	NPD6684	Approved
0.6628	Remote Similarity	NPD7521	Approved
0.6628	Remote Similarity	NPD7334	Approved
0.6628	Remote Similarity	NPD7146	Approved
0.6628	Remote Similarity	NPD6409	Approved
0.6628	Remote Similarity	NPD5330	Approved
0.6588	Remote Similarity	NPD4197	Approved
0.6559	Remote Similarity	NPD5290	Discontinued
0.6559	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD4696	Approved
0.6489	Remote Similarity	NPD5285	Approved
0.6489	Remote Similarity	NPD5286	Approved
0.6489	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD4700	Approved
0.6489	Remote Similarity	NPD7639	Approved
0.6477	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6903	Approved
0.6471	Remote Similarity	NPD4788	Approved
0.6463	Remote Similarity	NPD3617	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD6083	Phase 2
0.6437	Remote Similarity	NPD5205	Approved
0.6437	Remote Similarity	NPD4694	Approved
0.6437	Remote Similarity	NPD4693	Phase 3
0.6437	Remote Similarity	NPD4689	Approved
0.6437	Remote Similarity	NPD4519	Discontinued
0.6437	Remote Similarity	NPD5690	Phase 2
0.6437	Remote Similarity	NPD5280	Approved
0.6437	Remote Similarity	NPD4690	Approved
0.6437	Remote Similarity	NPD4138	Approved
0.6437	Remote Similarity	NPD4623	Approved
0.6437	Remote Similarity	NPD4688	Approved
0.6421	Remote Similarity	NPD5223	Approved
0.6413	Remote Similarity	NPD5210	Approved
0.6413	Remote Similarity	NPD4629	Approved
0.6404	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD6051	Approved
0.6404	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4225	Approved
0.6354	Remote Similarity	NPD5224	Approved
0.6354	Remote Similarity	NPD5211	Phase 2
0.6354	Remote Similarity	NPD5226	Approved
0.6354	Remote Similarity	NPD5225	Approved
0.6354	Remote Similarity	NPD4633	Approved
0.6333	Remote Similarity	NPD7136	Phase 2
0.6327	Remote Similarity	NPD7128	Approved
0.6327	Remote Similarity	NPD5739	Approved
0.6327	Remote Similarity	NPD6402	Approved
0.6327	Remote Similarity	NPD6675	Approved
0.6322	Remote Similarity	NPD1696	Phase 3
0.6308	Remote Similarity	NPD385	Approved
0.6308	Remote Similarity	NPD384	Approved
0.6304	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7900	Approved
0.6292	Remote Similarity	NPD5737	Approved
0.6292	Remote Similarity	NPD6672	Approved
0.6292	Remote Similarity	NPD4722	Approved
0.6292	Remote Similarity	NPD4723	Approved
0.6289	Remote Similarity	NPD4754	Approved
0.6289	Remote Similarity	NPD5174	Approved
0.6289	Remote Similarity	NPD5175	Approved
0.6282	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD4732	Discontinued
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5695	Phase 3
0.6235	Remote Similarity	NPD4139	Approved
0.6235	Remote Similarity	NPD4692	Approved
0.6224	Remote Similarity	NPD5141	Approved
0.622	Remote Similarity	NPD1346	Approved
0.6207	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4787	Phase 1
0.62	Remote Similarity	NPD6881	Approved
0.62	Remote Similarity	NPD6899	Approved
0.62	Remote Similarity	NPD7320	Approved
0.6196	Remote Similarity	NPD5778	Approved
0.6196	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD4767	Approved
0.6162	Remote Similarity	NPD4768	Approved
0.6154	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6372	Approved
0.6139	Remote Similarity	NPD6373	Approved
0.6125	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD7331	Phase 2
0.61	Remote Similarity	NPD5701	Approved
0.61	Remote Similarity	NPD6412	Phase 2
0.61	Remote Similarity	NPD5697	Approved
0.6087	Remote Similarity	NPD5284	Approved
0.6087	Remote Similarity	NPD8034	Phase 2
0.6087	Remote Similarity	NPD5281	Approved
0.6087	Remote Similarity	NPD8035	Phase 2
0.6082	Remote Similarity	NPD4159	Approved
0.6078	Remote Similarity	NPD7290	Approved
0.6078	Remote Similarity	NPD7102	Approved
0.6078	Remote Similarity	NPD6883	Approved
0.6076	Remote Similarity	NPD4137	Phase 3
0.6076	Remote Similarity	NPD15	Approved
0.6076	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD791	Approved
0.6071	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6098	Approved
0.6042	Remote Similarity	NPD5696	Approved
0.604	Remote Similarity	NPD4729	Approved
0.604	Remote Similarity	NPD5128	Approved
0.604	Remote Similarity	NPD4730	Approved
0.604	Remote Similarity	NPD6011	Approved
0.604	Remote Similarity	NPD5168	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD6869	Approved
0.6019	Remote Similarity	NPD8130	Phase 1
0.6019	Remote Similarity	NPD6847	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD4245	Approved
0.598	Remote Similarity	NPD6012	Approved
0.598	Remote Similarity	NPD6014	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