NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	468.25
Volume:	478.628
LogP:	5.243
LogD:	4.879
LogS:	-2.848
# Rotatable Bonds:	10
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	4.714
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.022
MDCK Permeability:	1.094922572519863e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.476
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	98.53409576416016%
Volume Distribution (VD):	1.762
Pgp-substrate:	1.2256144285202026%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.294
CYP2C9-inhibitor:	0.453
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.549
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	4.096
Half-life (T1/2):	0.029

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.645
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.516
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.553
Carcinogencity:	0.774
Eye Corrosion:	0.755
Eye Irritation:	0.483
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC477124

Natural Product ID:	NPC477124
*Common Name:**	Halisulfate 9
IUPAC Name:	[2-[2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-5-(5-oxo-2H-furan-3-yl)pentyl] hydrogen sulfate
Synonyms:	Halisulfate 9
Standard InCHIKey:	NFFYCHHMRWODEA-KYQCUNBSSA-N
Standard InCHI:	InChI=1S/C25H40O6S/c1-18-10-11-21-22(9-6-13-24(21,2)3)25(18,4)14-12-19(17-31-32(27,28)29)7-5-8-20-15-23(26)30-16-20/h9,15,18-19,21H,5-8,10-14,16-17H2,1-4H3,(H,27,28,29)/t18-,19?,21-,25-/m0/s1
SMILES:	C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CCC(CCCC3=CC(=O)OC3)COS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10368315
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33581	Fasciospongia sp.	Species	Thorectidae	Eukaryota	n.a.	at a depth of 1 m in Palau	2003-DEC	PMID[19178162]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	16	mm	PMID[19178162]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	14	mm	PMID[19178162]

☑ 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 NPC477124 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	160
0.1-0.2	1310
0.2-0.3	5661
0.3-0.4	16461
0.4-0.5	8291
0.5-0.6	7199
0.6-0.7	3121
0.7-0.8	463
0.8-0.85	23
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC318515
0.9059	High Similarity	NPC477122
0.878	High Similarity	NPC472440
0.8659	High Similarity	NPC471218
0.8571	High Similarity	NPC472442
0.8427	Intermediate Similarity	NPC324078
0.8353	Intermediate Similarity	NPC42586
0.8353	Intermediate Similarity	NPC474013
0.8353	Intermediate Similarity	NPC473251
0.8353	Intermediate Similarity	NPC189311
0.8353	Intermediate Similarity	NPC30984
0.8293	Intermediate Similarity	NPC242767
0.8256	Intermediate Similarity	NPC471219
0.8214	Intermediate Similarity	NPC200513
0.8214	Intermediate Similarity	NPC256112
0.8182	Intermediate Similarity	NPC476945
0.8182	Intermediate Similarity	NPC174342
0.8182	Intermediate Similarity	NPC470734
0.8182	Intermediate Similarity	NPC5509
0.814	Intermediate Similarity	NPC65661
0.8118	Intermediate Similarity	NPC311070
0.8118	Intermediate Similarity	NPC474193
0.8118	Intermediate Similarity	NPC12283
0.809	Intermediate Similarity	NPC78973
0.8068	Intermediate Similarity	NPC93411
0.8068	Intermediate Similarity	NPC226863
0.8049	Intermediate Similarity	NPC316500
0.8046	Intermediate Similarity	NPC131813
0.8043	Intermediate Similarity	NPC319692
0.8043	Intermediate Similarity	NPC325960
0.8023	Intermediate Similarity	NPC96055
0.8022	Intermediate Similarity	NPC104925
0.8022	Intermediate Similarity	NPC298973
0.8	Intermediate Similarity	NPC329842
0.7978	Intermediate Similarity	NPC177141
0.7931	Intermediate Similarity	NPC471795
0.7931	Intermediate Similarity	NPC106416
0.7931	Intermediate Similarity	NPC86316
0.7912	Intermediate Similarity	NPC7349
0.7907	Intermediate Similarity	NPC22611
0.7907	Intermediate Similarity	NPC476927
0.7907	Intermediate Similarity	NPC42476
0.7907	Intermediate Similarity	NPC324243
0.7907	Intermediate Similarity	NPC193198
0.7882	Intermediate Similarity	NPC25554
0.7882	Intermediate Similarity	NPC40228
0.7882	Intermediate Similarity	NPC229584
0.7882	Intermediate Similarity	NPC14203
0.7882	Intermediate Similarity	NPC170303
0.7865	Intermediate Similarity	NPC472810
0.7865	Intermediate Similarity	NPC472302
0.7865	Intermediate Similarity	NPC472809
0.7841	Intermediate Similarity	NPC220478
0.7831	Intermediate Similarity	NPC54996
0.7831	Intermediate Similarity	NPC189206
0.7826	Intermediate Similarity	NPC105490
0.7826	Intermediate Similarity	NPC469697
0.7816	Intermediate Similarity	NPC71626
0.7778	Intermediate Similarity	NPC168131
0.7778	Intermediate Similarity	NPC222244
0.7778	Intermediate Similarity	NPC284561
0.7778	Intermediate Similarity	NPC16349
0.7765	Intermediate Similarity	NPC469802
0.7765	Intermediate Similarity	NPC268827
0.7765	Intermediate Similarity	NPC195424
0.7765	Intermediate Similarity	NPC233332
0.7753	Intermediate Similarity	NPC476600
0.7753	Intermediate Similarity	NPC166857
0.7753	Intermediate Similarity	NPC471796
0.7753	Intermediate Similarity	NPC312561
0.7742	Intermediate Similarity	NPC276110
0.7742	Intermediate Similarity	NPC295347
0.7738	Intermediate Similarity	NPC184737
0.7727	Intermediate Similarity	NPC35933
0.7717	Intermediate Similarity	NPC115021
0.7717	Intermediate Similarity	NPC53555
0.7717	Intermediate Similarity	NPC475657
0.7701	Intermediate Similarity	NPC472377
0.7701	Intermediate Similarity	NPC49208
0.7701	Intermediate Similarity	NPC23748
0.7701	Intermediate Similarity	NPC474809
0.7692	Intermediate Similarity	NPC469595
0.7692	Intermediate Similarity	NPC280149
0.7692	Intermediate Similarity	NPC101651
0.7692	Intermediate Similarity	NPC232426
0.7692	Intermediate Similarity	NPC221111
0.7692	Intermediate Similarity	NPC159748
0.7692	Intermediate Similarity	NPC281942
0.7692	Intermediate Similarity	NPC212679
0.7692	Intermediate Similarity	NPC51486
0.7692	Intermediate Similarity	NPC273199
0.7692	Intermediate Similarity	NPC185587
0.7692	Intermediate Similarity	NPC477782
0.7692	Intermediate Similarity	NPC220454
0.7674	Intermediate Similarity	NPC282293
0.7674	Intermediate Similarity	NPC475944
0.7667	Intermediate Similarity	NPC474629
0.7667	Intermediate Similarity	NPC106332
0.7667	Intermediate Similarity	NPC472378
0.7662	Intermediate Similarity	NPC329698
0.766	Intermediate Similarity	NPC162346
0.7654	Intermediate Similarity	NPC257618
0.7647	Intermediate Similarity	NPC327674
0.764	Intermediate Similarity	NPC118266
0.764	Intermediate Similarity	NPC286153
0.7634	Intermediate Similarity	NPC477722
0.7634	Intermediate Similarity	NPC140277
0.7614	Intermediate Similarity	NPC149869
0.7614	Intermediate Similarity	NPC306951
0.7614	Intermediate Similarity	NPC471302
0.7614	Intermediate Similarity	NPC30486
0.7614	Intermediate Similarity	NPC471301
0.7609	Intermediate Similarity	NPC477783
0.7609	Intermediate Similarity	NPC177641
0.7609	Intermediate Similarity	NPC141831
0.7609	Intermediate Similarity	NPC234335
0.7609	Intermediate Similarity	NPC65513
0.7609	Intermediate Similarity	NPC472811
0.7604	Intermediate Similarity	NPC54705
0.7595	Intermediate Similarity	NPC472266
0.7586	Intermediate Similarity	NPC186276
0.7586	Intermediate Similarity	NPC471298
0.7586	Intermediate Similarity	NPC2524
0.7582	Intermediate Similarity	NPC251528
0.7582	Intermediate Similarity	NPC246028
0.7582	Intermediate Similarity	NPC293044
0.7579	Intermediate Similarity	NPC477719
0.7579	Intermediate Similarity	NPC208094
0.7579	Intermediate Similarity	NPC477718
0.7579	Intermediate Similarity	NPC51499
0.7561	Intermediate Similarity	NPC476489
0.7561	Intermediate Similarity	NPC476490
0.7556	Intermediate Similarity	NPC478104
0.7553	Intermediate Similarity	NPC293052
0.7553	Intermediate Similarity	NPC474909
0.7553	Intermediate Similarity	NPC281134
0.7553	Intermediate Similarity	NPC472441
0.7529	Intermediate Similarity	NPC209135
0.7529	Intermediate Similarity	NPC471220
0.7529	Intermediate Similarity	NPC474816
0.7527	Intermediate Similarity	NPC472812
0.7527	Intermediate Similarity	NPC205034
0.7527	Intermediate Similarity	NPC152778
0.7527	Intermediate Similarity	NPC162615
0.7527	Intermediate Similarity	NPC139692
0.7527	Intermediate Similarity	NPC38232
0.7527	Intermediate Similarity	NPC472303
0.7526	Intermediate Similarity	NPC472554
0.75	Intermediate Similarity	NPC181147
0.75	Intermediate Similarity	NPC4509
0.75	Intermediate Similarity	NPC471297
0.75	Intermediate Similarity	NPC182136
0.75	Intermediate Similarity	NPC8062
0.75	Intermediate Similarity	NPC325229
0.75	Intermediate Similarity	NPC275086
0.75	Intermediate Similarity	NPC30502
0.75	Intermediate Similarity	NPC97913
0.75	Intermediate Similarity	NPC278673
0.75	Intermediate Similarity	NPC92275
0.75	Intermediate Similarity	NPC310479
0.75	Intermediate Similarity	NPC302280
0.7474	Intermediate Similarity	NPC16967
0.7474	Intermediate Similarity	NPC29952
0.7474	Intermediate Similarity	NPC194132
0.7474	Intermediate Similarity	NPC190713
0.7474	Intermediate Similarity	NPC209297
0.7474	Intermediate Similarity	NPC475380
0.7473	Intermediate Similarity	NPC477128
0.7473	Intermediate Similarity	NPC24816
0.7473	Intermediate Similarity	NPC473879
0.7471	Intermediate Similarity	NPC327002
0.7468	Intermediate Similarity	NPC242945
0.7468	Intermediate Similarity	NPC259156
0.7449	Intermediate Similarity	NPC472552
0.7449	Intermediate Similarity	NPC11956
0.7447	Intermediate Similarity	NPC470255
0.7447	Intermediate Similarity	NPC477130
0.7447	Intermediate Similarity	NPC477129
0.7447	Intermediate Similarity	NPC166143
0.7447	Intermediate Similarity	NPC84893
0.7447	Intermediate Similarity	NPC120351
0.7447	Intermediate Similarity	NPC471994
0.7447	Intermediate Similarity	NPC476415
0.7444	Intermediate Similarity	NPC474062
0.7444	Intermediate Similarity	NPC102996
0.7442	Intermediate Similarity	NPC44083
0.7442	Intermediate Similarity	NPC150646
0.7442	Intermediate Similarity	NPC153987
0.7423	Intermediate Similarity	NPC324841
0.7423	Intermediate Similarity	NPC477720
0.7423	Intermediate Similarity	NPC476299
0.7423	Intermediate Similarity	NPC474012
0.7423	Intermediate Similarity	NPC38855
0.7423	Intermediate Similarity	NPC471413
0.7423	Intermediate Similarity	NPC477721
0.7423	Intermediate Similarity	NPC477716
0.7419	Intermediate Similarity	NPC177037
0.7419	Intermediate Similarity	NPC472814
0.7419	Intermediate Similarity	NPC470113
0.7419	Intermediate Similarity	NPC72845

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 NPC477124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	1479
0.2-0.3	4261
0.3-0.4	2377
0.4-0.5	542
0.5-0.6	271
0.6-0.7	86
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8214	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6051	Approved
0.732	Intermediate Similarity	NPD7638	Approved
0.7283	Intermediate Similarity	NPD5737	Approved
0.7283	Intermediate Similarity	NPD6672	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1694	Approved
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7053	Intermediate Similarity	NPD5693	Phase 1
0.7033	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8039	Approved
0.697	Remote Similarity	NPD4225	Approved
0.6907	Remote Similarity	NPD7748	Approved
0.6869	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD6904	Approved
0.6842	Remote Similarity	NPD6080	Approved
0.6842	Remote Similarity	NPD6673	Approved
0.6837	Remote Similarity	NPD5695	Phase 3
0.6804	Remote Similarity	NPD6399	Phase 3
0.6762	Remote Similarity	NPD6686	Approved
0.6735	Remote Similarity	NPD7900	Approved
0.6735	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD6050	Approved
0.67	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD5692	Phase 3
0.6562	Remote Similarity	NPD5208	Approved
0.6531	Remote Similarity	NPD5694	Approved
0.6526	Remote Similarity	NPD6098	Approved
0.6489	Remote Similarity	NPD3666	Approved
0.6489	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6484	Remote Similarity	NPD4195	Approved
0.6458	Remote Similarity	NPD3573	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD5739	Approved
0.6415	Remote Similarity	NPD6675	Approved
0.6415	Remote Similarity	NPD6402	Approved
0.6415	Remote Similarity	NPD7128	Approved
0.6404	Remote Similarity	NPD6942	Approved
0.6404	Remote Similarity	NPD7339	Approved
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7327	Approved
0.6372	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD5281	Approved
0.6355	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4623	Approved
0.6354	Remote Similarity	NPD3618	Phase 1
0.6354	Remote Similarity	NPD4519	Discontinued
0.6341	Remote Similarity	NPD4194	Approved
0.6341	Remote Similarity	NPD4191	Approved
0.6341	Remote Similarity	NPD4192	Approved
0.6341	Remote Similarity	NPD4193	Approved
0.6333	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5328	Approved
0.6327	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4753	Phase 2
0.6316	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD7516	Approved
0.6304	Remote Similarity	NPD7645	Phase 2
0.6296	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6277	Remote Similarity	NPD3667	Approved
0.6277	Remote Similarity	NPD4221	Approved
0.6277	Remote Similarity	NPD4223	Phase 3
0.6273	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5785	Approved
0.6261	Remote Similarity	NPD8377	Approved
0.6261	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6404	Discontinued
0.625	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD4243	Approved
0.625	Remote Similarity	NPD5329	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6238	Remote Similarity	NPD6001	Approved
0.6237	Remote Similarity	NPD7525	Registered
0.6237	Remote Similarity	NPD4695	Discontinued
0.6226	Remote Similarity	NPD6052	Approved
0.6216	Remote Similarity	NPD6053	Discontinued
0.6211	Remote Similarity	NPD6695	Phase 3
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD7503	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD8033	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.6204	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD6411	Approved
0.62	Remote Similarity	NPD6079	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6186	Remote Similarity	NPD5279	Phase 3
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6176	Remote Similarity	NPD5654	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD4197	Approved
0.6146	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD6650	Approved
0.6126	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD7732	Phase 3
0.6111	Remote Similarity	NPD4785	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD6008	Approved
0.6111	Remote Similarity	NPD4784	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.61	Remote Similarity	NPD46	Approved
0.61	Remote Similarity	NPD6698	Approved
0.61	Remote Similarity	NPD7838	Discovery
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6078	Remote Similarity	NPD5707	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD5959	Approved
0.6055	Remote Similarity	NPD6412	Phase 2
0.6044	Remote Similarity	NPD8264	Approved
0.604	Remote Similarity	NPD8035	Phase 2
0.604	Remote Similarity	NPD8034	Phase 2
0.6023	Remote Similarity	NPD4137	Phase 3
0.6022	Remote Similarity	NPD3617	Approved
0.6022	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4690	Approved
0.602	Remote Similarity	NPD5690	Phase 2
0.602	Remote Similarity	NPD5205	Approved
0.602	Remote Similarity	NPD4138	Approved
0.602	Remote Similarity	NPD4689	Approved
0.602	Remote Similarity	NPD4693	Phase 3
0.602	Remote Similarity	NPD4694	Approved
0.602	Remote Similarity	NPD4688	Approved
0.602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5280	Approved
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD5210	Approved
0.6019	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.598	Remote Similarity	NPD4202	Approved
0.5978	Remote Similarity	NPD6933	Approved
0.5962	Remote Similarity	NPD4697	Phase 3
0.5962	Remote Similarity	NPD5221	Approved
0.5962	Remote Similarity	NPD5222	Approved
0.5962	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7614	Phase 1
0.596	Remote Similarity	NPD7524	Approved
0.596	Remote Similarity	NPD7750	Discontinued
0.596	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6929	Approved
0.5955	Remote Similarity	NPD4691	Approved
0.5955	Remote Similarity	NPD4747	Approved
0.5934	Remote Similarity	NPD5733	Approved
0.5918	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6868	Approved
0.5909	Remote Similarity	NPD6614	Approved
0.5905	Remote Similarity	NPD4755	Approved
0.5905	Remote Similarity	NPD5173	Approved
0.5895	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6931	Approved
0.5895	Remote Similarity	NPD6930	Phase 2
0.5876	Remote Similarity	NPD7154	Phase 3
0.5876	Remote Similarity	NPD5362	Discontinued
0.587	Remote Similarity	NPD4190	Phase 3
0.587	Remote Similarity	NPD5275	Approved
0.5862	Remote Similarity	NPD6317	Approved
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD8029	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