NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	538.28
Volume:	541.895
LogP:	2.5
LogD:	1.066
LogS:	-3.39
# Rotatable Bonds:	11
TPSA:	131.5
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	5.454
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.213
MDCK Permeability:	8.153812814271078e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.823
Plasma Protein Binding (PPB):	35.35329055786133%
Volume Distribution (VD):	1.066
Pgp-substrate:	46.86023712158203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.271
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.647

ADMET: Excretion

Clearance (CL):	3.487
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.167
Skin Sensitization:	0.459
Carcinogencity:	0.343
Eye Corrosion:	0.621
Eye Irritation:	0.208
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC477441

Natural Product ID:	NPC477441
*Common Name:**	(8S,13S)-7-Oxo-9,13-epoxylabdane-3alpha,6beta,15,19-tetraol tetraacetate
IUPAC Name:	2-[(2'S,3R,4S,4aS,5S,7S,8R,8aS)-3,5-diacetyloxy-4-(acetyloxymethyl)-2',4,7,8a-tetramethyl-6-oxospiro[1,2,3,4a,5,7-hexahydronaphthalene-8,5'-oxolane]-2'-yl]ethyl acetate
Synonyms:
Standard InCHIKey:	WJSWULVNRNZNEC-CKSXMQKCSA-N
Standard InCHI:	InChI=1S/C28H42O10/c1-16-22(33)23(37-20(5)32)24-26(7,15-35-18(3)30)21(36-19(4)31)9-10-27(24,8)28(16)12-11-25(6,38-28)13-14-34-17(2)29/h16,21,23-24H,9-15H2,1-8H3/t16-,21-,23-,24+,25+,26+,27+,28-/m1/s1
SMILES:	C[C@@H]1C(=O)[C@H]([C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CCOC(=O)C)(CC[C@H]([C@]2(C)COC(=O)C)OC(=O)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122186909
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
NPO33600	Leonurus macranthus	Species	Lamiaceae	Eukaryota	aerial parts	Huanren, Liaoning Province, China	2013-AUG	PMID[26348503]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	48100	nM	PMID[26348503]

☑ 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 NPC477441 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	447
0.1-0.2	3752
0.2-0.3	8541
0.3-0.4	13688
0.4-0.5	6484
0.5-0.6	6420
0.6-0.7	2909
0.7-0.8	419
0.8-0.85	24
0.85-0.9	6
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC477444
0.9524	High Similarity	NPC477433
0.9524	High Similarity	NPC477442
0.9412	High Similarity	NPC216137
0.9405	High Similarity	NPC477443
0.9405	High Similarity	NPC477440
0.8864	High Similarity	NPC474379
0.881	High Similarity	NPC477434
0.8588	High Similarity	NPC65133
0.8554	High Similarity	NPC134227
0.8554	High Similarity	NPC125366
0.8488	Intermediate Similarity	NPC477445
0.8272	Intermediate Similarity	NPC55508
0.8261	Intermediate Similarity	NPC62407
0.8261	Intermediate Similarity	NPC287354
0.8256	Intermediate Similarity	NPC476721
0.8202	Intermediate Similarity	NPC471221
0.8193	Intermediate Similarity	NPC143250
0.8182	Intermediate Similarity	NPC476717
0.8161	Intermediate Similarity	NPC475689
0.8148	Intermediate Similarity	NPC474755
0.8148	Intermediate Similarity	NPC109510
0.8111	Intermediate Similarity	NPC471459
0.8111	Intermediate Similarity	NPC67653
0.8023	Intermediate Similarity	NPC328639
0.8023	Intermediate Similarity	NPC329490
0.8	Intermediate Similarity	NPC221993
0.7978	Intermediate Similarity	NPC83242
0.7976	Intermediate Similarity	NPC471151
0.7955	Intermediate Similarity	NPC237938
0.7955	Intermediate Similarity	NPC219535
0.7955	Intermediate Similarity	NPC9060
0.7955	Intermediate Similarity	NPC181871
0.7865	Intermediate Similarity	NPC473350
0.7865	Intermediate Similarity	NPC474572
0.7865	Intermediate Similarity	NPC477205
0.7857	Intermediate Similarity	NPC474020
0.7849	Intermediate Similarity	NPC476189
0.7841	Intermediate Similarity	NPC15091
0.7802	Intermediate Similarity	NPC236459
0.7802	Intermediate Similarity	NPC476435
0.7802	Intermediate Similarity	NPC226491
0.7802	Intermediate Similarity	NPC477614
0.7791	Intermediate Similarity	NPC275243
0.7778	Intermediate Similarity	NPC243746
0.7778	Intermediate Similarity	NPC88469
0.7766	Intermediate Similarity	NPC309127
0.7766	Intermediate Similarity	NPC247877
0.7766	Intermediate Similarity	NPC477495
0.7765	Intermediate Similarity	NPC307865
0.7753	Intermediate Similarity	NPC473336
0.7753	Intermediate Similarity	NPC473299
0.7753	Intermediate Similarity	NPC471044
0.7727	Intermediate Similarity	NPC13494
0.7717	Intermediate Similarity	NPC61688
0.7717	Intermediate Similarity	NPC200580
0.7708	Intermediate Similarity	NPC266417
0.7684	Intermediate Similarity	NPC217329
0.767	Intermediate Similarity	NPC157476
0.7647	Intermediate Similarity	NPC471046
0.7647	Intermediate Similarity	NPC474242
0.7634	Intermediate Similarity	NPC475211
0.7634	Intermediate Similarity	NPC88337
0.7629	Intermediate Similarity	NPC253995
0.7624	Intermediate Similarity	NPC201908
0.7624	Intermediate Similarity	NPC176949
0.7614	Intermediate Similarity	NPC470154
0.7614	Intermediate Similarity	NPC475743
0.7609	Intermediate Similarity	NPC3032
0.7609	Intermediate Similarity	NPC131104
0.7609	Intermediate Similarity	NPC473319
0.7604	Intermediate Similarity	NPC193785
0.7604	Intermediate Similarity	NPC477264
0.7586	Intermediate Similarity	NPC474754
0.7582	Intermediate Similarity	NPC120395
0.7582	Intermediate Similarity	NPC248216
0.7579	Intermediate Similarity	NPC470424
0.7576	Intermediate Similarity	NPC471254
0.7556	Intermediate Similarity	NPC50438
0.7556	Intermediate Similarity	NPC105895
0.7553	Intermediate Similarity	NPC475878
0.7553	Intermediate Similarity	NPC470230
0.7528	Intermediate Similarity	NPC477446
0.7528	Intermediate Similarity	NPC470155
0.7528	Intermediate Similarity	NPC477447
0.7526	Intermediate Similarity	NPC470632
0.7526	Intermediate Similarity	NPC74466
0.75	Intermediate Similarity	NPC473406
0.75	Intermediate Similarity	NPC471253
0.75	Intermediate Similarity	NPC470920
0.75	Intermediate Similarity	NPC469985
0.75	Intermediate Similarity	NPC1882
0.7475	Intermediate Similarity	NPC298266
0.7475	Intermediate Similarity	NPC236585
0.7475	Intermediate Similarity	NPC259654
0.7473	Intermediate Similarity	NPC476715
0.7471	Intermediate Similarity	NPC475725
0.7449	Intermediate Similarity	NPC474724
0.7449	Intermediate Similarity	NPC474793
0.7447	Intermediate Similarity	NPC470114
0.7426	Intermediate Similarity	NPC327093
0.7423	Intermediate Similarity	NPC163685
0.7423	Intermediate Similarity	NPC475765
0.7423	Intermediate Similarity	NPC116683
0.7423	Intermediate Similarity	NPC235109
0.7423	Intermediate Similarity	NPC476728
0.7419	Intermediate Similarity	NPC476379
0.7416	Intermediate Similarity	NPC470156
0.7416	Intermediate Similarity	NPC71541
0.7407	Intermediate Similarity	NPC84562
0.7404	Intermediate Similarity	NPC100908
0.74	Intermediate Similarity	NPC275990
0.74	Intermediate Similarity	NPC470172
0.7396	Intermediate Similarity	NPC477439
0.7391	Intermediate Similarity	NPC474008
0.7391	Intermediate Similarity	NPC474215
0.7391	Intermediate Similarity	NPC475729
0.7391	Intermediate Similarity	NPC302111
0.7386	Intermediate Similarity	NPC73013
0.7383	Intermediate Similarity	NPC173686
0.7383	Intermediate Similarity	NPC16081
0.7383	Intermediate Similarity	NPC213084
0.7383	Intermediate Similarity	NPC475490
0.7383	Intermediate Similarity	NPC190185
0.7379	Intermediate Similarity	NPC153587
0.7379	Intermediate Similarity	NPC289702
0.7379	Intermediate Similarity	NPC208461
0.7379	Intermediate Similarity	NPC316930
0.7374	Intermediate Similarity	NPC293890
0.7368	Intermediate Similarity	NPC476934
0.7368	Intermediate Similarity	NPC52756
0.7363	Intermediate Similarity	NPC319909
0.7363	Intermediate Similarity	NPC34984
0.7363	Intermediate Similarity	NPC25037
0.7358	Intermediate Similarity	NPC94509
0.7353	Intermediate Similarity	NPC50535
0.7347	Intermediate Similarity	NPC253586
0.7347	Intermediate Similarity	NPC469810
0.7347	Intermediate Similarity	NPC474921
0.7347	Intermediate Similarity	NPC96839
0.734	Intermediate Similarity	NPC24705
0.734	Intermediate Similarity	NPC471043
0.734	Intermediate Similarity	NPC56962
0.7333	Intermediate Similarity	NPC477284
0.7327	Intermediate Similarity	NPC87927
0.732	Intermediate Similarity	NPC82633
0.732	Intermediate Similarity	NPC477437
0.732	Intermediate Similarity	NPC305808
0.732	Intermediate Similarity	NPC477438
0.732	Intermediate Similarity	NPC17336
0.732	Intermediate Similarity	NPC470229
0.7315	Intermediate Similarity	NPC146432
0.7315	Intermediate Similarity	NPC470778
0.7312	Intermediate Similarity	NPC263802
0.7312	Intermediate Similarity	NPC239938
0.7308	Intermediate Similarity	NPC16657
0.7308	Intermediate Similarity	NPC204652
0.7308	Intermediate Similarity	NPC320475
0.7308	Intermediate Similarity	NPC321661
0.7303	Intermediate Similarity	NPC472951
0.7303	Intermediate Similarity	NPC472943
0.7303	Intermediate Similarity	NPC471217
0.7303	Intermediate Similarity	NPC471216
0.73	Intermediate Similarity	NPC476478
0.73	Intermediate Similarity	NPC46848
0.7294	Intermediate Similarity	NPC123122
0.7292	Intermediate Similarity	NPC228700
0.7292	Intermediate Similarity	NPC147272
0.7292	Intermediate Similarity	NPC472148
0.7292	Intermediate Similarity	NPC472147
0.729	Intermediate Similarity	NPC143268
0.729	Intermediate Similarity	NPC477465
0.729	Intermediate Similarity	NPC268238
0.729	Intermediate Similarity	NPC299849
0.729	Intermediate Similarity	NPC45218
0.729	Intermediate Similarity	NPC470116
0.729	Intermediate Similarity	NPC323821
0.729	Intermediate Similarity	NPC470115
0.7282	Intermediate Similarity	NPC203974
0.7282	Intermediate Similarity	NPC86852
0.7282	Intermediate Similarity	NPC251824
0.7273	Intermediate Similarity	NPC476294
0.7273	Intermediate Similarity	NPC472144
0.7273	Intermediate Similarity	NPC471038
0.7273	Intermediate Similarity	NPC17183
0.7263	Intermediate Similarity	NPC185529
0.7263	Intermediate Similarity	NPC77756
0.7263	Intermediate Similarity	NPC472146
0.7255	Intermediate Similarity	NPC473701
0.7255	Intermediate Similarity	NPC473526
0.7255	Intermediate Similarity	NPC47281
0.7253	Intermediate Similarity	NPC327451
0.7248	Intermediate Similarity	NPC297179
0.7245	Intermediate Similarity	NPC329910
0.7245	Intermediate Similarity	NPC219353
0.7245	Intermediate Similarity	NPC475785
0.7238	Intermediate Similarity	NPC470622
0.7234	Intermediate Similarity	NPC56777
0.7234	Intermediate Similarity	NPC201607
0.7222	Intermediate Similarity	NPC89929

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 NPC477441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	461
0.1-0.2	3801
0.2-0.3	3170
0.3-0.4	1024
0.4-0.5	345
0.5-0.6	197
0.6-0.7	137
0.7-0.8	15
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
0.7475	Intermediate Similarity	NPD1700	Approved
0.7379	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6118	Approved
0.7079	Intermediate Similarity	NPD6114	Approved
0.7079	Intermediate Similarity	NPD6697	Approved
0.7079	Intermediate Similarity	NPD6115	Approved
0.6977	Remote Similarity	NPD5777	Approved
0.6966	Remote Similarity	NPD6116	Phase 1
0.6932	Remote Similarity	NPD3703	Phase 2
0.6857	Remote Similarity	NPD7128	Approved
0.6857	Remote Similarity	NPD6675	Approved
0.6857	Remote Similarity	NPD6402	Approved
0.6857	Remote Similarity	NPD5739	Approved
0.6854	Remote Similarity	NPD6117	Approved
0.6822	Remote Similarity	NPD6373	Approved
0.6822	Remote Similarity	NPD6372	Approved
0.6814	Remote Similarity	NPD6319	Approved
0.6754	Remote Similarity	NPD6921	Approved
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD7320	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6724	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6697	Remote Similarity	NPD6649	Approved
0.6697	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6629	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD229	Approved
0.661	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD7078	Approved
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6604	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3702	Approved
0.6555	Remote Similarity	NPD7736	Approved
0.6552	Remote Similarity	NPD6370	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6869	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD8328	Phase 3
0.6489	Remote Similarity	NPD1780	Approved
0.6489	Remote Similarity	NPD1779	Approved
0.6481	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6015	Approved
0.6466	Remote Similarity	NPD6016	Approved
0.6422	Remote Similarity	NPD6011	Approved
0.641	Remote Similarity	NPD5988	Approved
0.6404	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6364	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8035	Phase 2
0.6337	Remote Similarity	NPD8034	Phase 2
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4789	Approved
0.6283	Remote Similarity	NPD4632	Approved
0.6279	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD5360	Phase 3
0.625	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6081	Approved
0.6218	Remote Similarity	NPD7604	Phase 2
0.6216	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7900	Approved
0.6214	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4224	Phase 2
0.619	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD5983	Phase 2
0.6174	Remote Similarity	NPD6274	Approved
0.6162	Remote Similarity	NPD6098	Approved
0.6161	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD6033	Approved
0.6147	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6904	Approved
0.6139	Remote Similarity	NPD6080	Approved
0.6139	Remote Similarity	NPD6673	Approved
0.6117	Remote Similarity	NPD6399	Phase 3
0.6116	Remote Similarity	NPD6336	Discontinued
0.6111	Remote Similarity	NPD8301	Approved
0.6111	Remote Similarity	NPD4244	Approved
0.6111	Remote Similarity	NPD4245	Approved
0.6111	Remote Similarity	NPD8300	Approved
0.61	Remote Similarity	NPD3573	Approved
0.6092	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5285	Approved
0.6075	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD4696	Approved
0.6075	Remote Similarity	NPD5286	Approved
0.6068	Remote Similarity	NPD6335	Approved
0.6061	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7748	Approved
0.605	Remote Similarity	NPD6908	Approved
0.605	Remote Similarity	NPD6909	Approved
0.6038	Remote Similarity	NPD7902	Approved
0.602	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3669	Approved
0.6	Remote Similarity	NPD3698	Phase 2
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5983	Remote Similarity	NPD6317	Approved
0.5981	Remote Similarity	NPD5696	Approved
0.5981	Remote Similarity	NPD7638	Approved
0.5968	Remote Similarity	NPD7319	Approved
0.5963	Remote Similarity	NPD5225	Approved
0.5963	Remote Similarity	NPD4633	Approved
0.5963	Remote Similarity	NPD5226	Approved
0.5963	Remote Similarity	NPD5224	Approved
0.5963	Remote Similarity	NPD5211	Phase 2
0.5946	Remote Similarity	NPD4767	Approved
0.5946	Remote Similarity	NPD4768	Approved
0.5932	Remote Similarity	NPD6314	Approved
0.5932	Remote Similarity	NPD6313	Approved
0.5926	Remote Similarity	NPD7639	Approved
0.5926	Remote Similarity	NPD7640	Approved
0.5909	Remote Similarity	NPD5174	Approved
0.5909	Remote Similarity	NPD5175	Approved
0.5905	Remote Similarity	NPD5282	Discontinued
0.5897	Remote Similarity	NPD6868	Approved
0.5882	Remote Similarity	NPD6903	Approved
0.5882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6928	Phase 2
0.5872	Remote Similarity	NPD5223	Approved
0.587	Remote Similarity	NPD4758	Discontinued
0.5865	Remote Similarity	NPD6050	Approved
0.5865	Remote Similarity	NPD6411	Approved
0.5865	Remote Similarity	NPD5693	Phase 1
0.5865	Remote Similarity	NPD7515	Phase 2
0.5856	Remote Similarity	NPD5141	Approved
0.5854	Remote Similarity	NPD7507	Approved
0.5841	Remote Similarity	NPD4729	Approved
0.5841	Remote Similarity	NPD4730	Approved
0.5833	Remote Similarity	NPD3671	Phase 1
0.5833	Remote Similarity	NPD5364	Discontinued
0.5825	Remote Similarity	NPD5328	Approved
0.5824	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7632	Discontinued
0.581	Remote Similarity	NPD5779	Approved
0.581	Remote Similarity	NPD5778	Approved
0.5794	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5222	Approved
0.5794	Remote Similarity	NPD4697	Phase 3
0.5794	Remote Similarity	NPD5221	Approved
0.5785	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.578	Remote Similarity	NPD8418	Phase 2
0.5769	Remote Similarity	NPD5692	Phase 3
0.5766	Remote Similarity	NPD4754	Approved
0.5761	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD1694	Approved
0.5741	Remote Similarity	NPD5173	Approved
0.5739	Remote Similarity	NPD5248	Approved
0.5739	Remote Similarity	NPD5250	Approved
0.5739	Remote Similarity	NPD5247	Approved
0.5739	Remote Similarity	NPD5251	Approved
0.5739	Remote Similarity	NPD5249	Phase 3
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD5694	Approved
0.5714	Remote Similarity	NPD6079	Approved
0.5702	Remote Similarity	NPD6686	Approved
0.5702	Remote Similarity	NPD5128	Approved
0.5688	Remote Similarity	NPD4225	Approved
0.5676	Remote Similarity	NPD8086	Approved
0.5676	Remote Similarity	NPD8082	Approved
0.5676	Remote Similarity	NPD8139	Approved
0.5676	Remote Similarity	NPD8085	Approved
0.5676	Remote Similarity	NPD8138	Approved
0.5676	Remote Similarity	NPD8083	Approved
0.5676	Remote Similarity	NPD8084	Approved
0.5673	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6101	Approved
0.566	Remote Similarity	NPD8171	Discontinued

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