NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	344.865
LogP:	3.083
LogD:	2.756
LogS:	-4.242
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	5.151
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	3.040803494513966e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.138
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	69.29889678955078%
Volume Distribution (VD):	0.791
Pgp-substrate:	33.00472640991211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	9.019
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.479
Rat Oral Acute Toxicity:	0.88
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.326
Carcinogencity:	0.956
Eye Corrosion:	0.018
Eye Irritation:	0.038
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC477653

Natural Product ID:	NPC477653
*Common Name:**	Hawaiinolide A
IUPAC Name:	(1R,2S,6S,7R,10S,11S,14S)-6-ethenyl-10-hydroxy-1,11-dimethyl-5-methylidene-13-oxatetracyclo[8.6.0.02,7.011,14]hexadecane-9,12-dione
Synonyms:
Standard InCHIKey:	RIIIZSAGFOLSAE-XTIVUVSQSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-5-12-11(2)6-7-14-13(12)10-15(21)20(23)18(14,3)9-8-16-19(20,4)17(22)24-16/h5,12-14,16,23H,1-2,6-10H2,3-4H3/t12-,13+,14+,16+,18-,19-,20+/m1/s1
SMILES:	C[C@]12CC[C@H]3[C@@]([C@@]1(C(=O)C[C@@H]4[C@@H]2CCC(=C)[C@H]4C=C)O)(C(=O)O3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90683060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO33607	Paraconiothyrium hawaiiense	Species	Didymosphaeriaceae	Eukaryota	isolated from a Septobasidium sp.-infected Diaspidiotus sp	Cang Mountain, Dali, Yunnan Province, China	2011-AUG	PMID[24882446]

☑ 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	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7480	nM	PMID[24882446]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6230	nM	PMID[24882446]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7430	nM	PMID[24882446]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2840	nM	PMID[24882446]
NPT2	Others	Unspecified		IC50	=	4260	nM	PMID[24882446]

☑ 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 NPC477653 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	238
0.1-0.2	1752
0.2-0.3	5544
0.3-0.4	10680
0.4-0.5	11783
0.5-0.6	6607
0.6-0.7	4894
0.7-0.8	1174
0.8-0.85	24
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8673	High Similarity	NPC477656
0.8571	High Similarity	NPC474724
0.8526	High Similarity	NPC198054
0.8485	Intermediate Similarity	NPC477655
0.84	Intermediate Similarity	NPC477052
0.84	Intermediate Similarity	NPC477051
0.84	Intermediate Similarity	NPC477053
0.835	Intermediate Similarity	NPC201908
0.835	Intermediate Similarity	NPC176949
0.8317	Intermediate Similarity	NPC477054
0.8247	Intermediate Similarity	NPC199543
0.8218	Intermediate Similarity	NPC46848
0.82	Intermediate Similarity	NPC78427
0.82	Intermediate Similarity	NPC89099
0.82	Intermediate Similarity	NPC16911
0.8163	Intermediate Similarity	NPC469982
0.8163	Intermediate Similarity	NPC475118
0.8163	Intermediate Similarity	NPC47853
0.8155	Intermediate Similarity	NPC84928
0.8144	Intermediate Similarity	NPC476934
0.8137	Intermediate Similarity	NPC275990
0.8137	Intermediate Similarity	NPC88203
0.8137	Intermediate Similarity	NPC76866
0.8137	Intermediate Similarity	NPC304832
0.8137	Intermediate Similarity	NPC148628
0.8137	Intermediate Similarity	NPC246736
0.8137	Intermediate Similarity	NPC286519
0.8137	Intermediate Similarity	NPC214946
0.8119	Intermediate Similarity	NPC287676
0.8119	Intermediate Similarity	NPC293866
0.8119	Intermediate Similarity	NPC293890
0.8113	Intermediate Similarity	NPC100908
0.81	Intermediate Similarity	NPC10864
0.81	Intermediate Similarity	NPC253586
0.8095	Intermediate Similarity	NPC289702
0.8095	Intermediate Similarity	NPC208461
0.8081	Intermediate Similarity	NPC470232
0.8081	Intermediate Similarity	NPC217329
0.8081	Intermediate Similarity	NPC470229
0.8058	Intermediate Similarity	NPC216114
0.8041	Intermediate Similarity	NPC46758
0.8039	Intermediate Similarity	NPC118964
0.8039	Intermediate Similarity	NPC163963
0.8039	Intermediate Similarity	NPC52899
0.8039	Intermediate Similarity	NPC289148
0.802	Intermediate Similarity	NPC471038
0.802	Intermediate Similarity	NPC38296
0.802	Intermediate Similarity	NPC162459
0.802	Intermediate Similarity	NPC472028
0.802	Intermediate Similarity	NPC38471
0.802	Intermediate Similarity	NPC119036
0.802	Intermediate Similarity	NPC20479
0.802	Intermediate Similarity	NPC98837
0.802	Intermediate Similarity	NPC28864
0.8	Intermediate Similarity	NPC219353
0.8	Intermediate Similarity	NPC329910
0.7981	Intermediate Similarity	NPC47281
0.7981	Intermediate Similarity	NPC98603
0.798	Intermediate Similarity	NPC470385
0.798	Intermediate Similarity	NPC470386
0.7941	Intermediate Similarity	NPC94906
0.7941	Intermediate Similarity	NPC108371
0.7938	Intermediate Similarity	NPC59682
0.7938	Intermediate Similarity	NPC471043
0.7921	Intermediate Similarity	NPC476878
0.7921	Intermediate Similarity	NPC476879
0.7909	Intermediate Similarity	NPC207217
0.7905	Intermediate Similarity	NPC200957
0.7905	Intermediate Similarity	NPC37600
0.7905	Intermediate Similarity	NPC28791
0.7905	Intermediate Similarity	NPC295366
0.7905	Intermediate Similarity	NPC138908
0.7905	Intermediate Similarity	NPC50535
0.79	Intermediate Similarity	NPC210214
0.7895	Intermediate Similarity	NPC224345
0.7885	Intermediate Similarity	NPC139347
0.7885	Intermediate Similarity	NPC87927
0.7885	Intermediate Similarity	NPC478057
0.7885	Intermediate Similarity	NPC469985
0.787	Intermediate Similarity	NPC171888
0.787	Intermediate Similarity	NPC146945
0.7864	Intermediate Similarity	NPC471790
0.7864	Intermediate Similarity	NPC253886
0.7864	Intermediate Similarity	NPC111292
0.7864	Intermediate Similarity	NPC295276
0.7864	Intermediate Similarity	NPC121218
0.7857	Intermediate Similarity	NPC153853
0.785	Intermediate Similarity	NPC204652
0.785	Intermediate Similarity	NPC16657
0.7843	Intermediate Similarity	NPC191565
0.7843	Intermediate Similarity	NPC17183
0.7843	Intermediate Similarity	NPC474793
0.783	Intermediate Similarity	NPC166993
0.783	Intermediate Similarity	NPC251824
0.783	Intermediate Similarity	NPC86852
0.7822	Intermediate Similarity	NPC13949
0.7822	Intermediate Similarity	NPC470387
0.7822	Intermediate Similarity	NPC200054
0.7822	Intermediate Similarity	NPC29410
0.7822	Intermediate Similarity	NPC223169
0.7822	Intermediate Similarity	NPC473964
0.781	Intermediate Similarity	NPC29705
0.78	Intermediate Similarity	NPC272635
0.78	Intermediate Similarity	NPC78580
0.78	Intermediate Similarity	NPC169751
0.78	Intermediate Similarity	NPC23621
0.78	Intermediate Similarity	NPC184006
0.7798	Intermediate Similarity	NPC40608
0.7789	Intermediate Similarity	NPC97505
0.7788	Intermediate Similarity	NPC170615
0.7788	Intermediate Similarity	NPC124544
0.7788	Intermediate Similarity	NPC164551
0.7778	Intermediate Similarity	NPC211403
0.7778	Intermediate Similarity	NPC474567
0.7778	Intermediate Similarity	NPC198242
0.7778	Intermediate Similarity	NPC471901
0.7778	Intermediate Similarity	NPC250753
0.7778	Intermediate Similarity	NPC470230
0.7767	Intermediate Similarity	NPC475156
0.7767	Intermediate Similarity	NPC37047
0.7767	Intermediate Similarity	NPC180733
0.7767	Intermediate Similarity	NPC473576
0.7767	Intermediate Similarity	NPC41971
0.7767	Intermediate Similarity	NPC470388
0.7767	Intermediate Similarity	NPC55503
0.7767	Intermediate Similarity	NPC156324
0.7767	Intermediate Similarity	NPC472972
0.7757	Intermediate Similarity	NPC273155
0.7757	Intermediate Similarity	NPC231278
0.7757	Intermediate Similarity	NPC112895
0.7757	Intermediate Similarity	NPC218123
0.7757	Intermediate Similarity	NPC153587
0.7755	Intermediate Similarity	NPC194642
0.7755	Intermediate Similarity	NPC475108
0.7745	Intermediate Similarity	NPC89225
0.7745	Intermediate Similarity	NPC26413
0.7745	Intermediate Similarity	NPC111187
0.7745	Intermediate Similarity	NPC473963
0.7745	Intermediate Similarity	NPC190080
0.7736	Intermediate Similarity	NPC222833
0.7736	Intermediate Similarity	NPC472655
0.7727	Intermediate Similarity	NPC208998
0.7727	Intermediate Similarity	NPC7921
0.7723	Intermediate Similarity	NPC263135
0.7723	Intermediate Similarity	NPC195715
0.7723	Intermediate Similarity	NPC272617
0.7723	Intermediate Similarity	NPC197158
0.7723	Intermediate Similarity	NPC288906
0.7723	Intermediate Similarity	NPC98639
0.7723	Intermediate Similarity	NPC474727
0.7723	Intermediate Similarity	NPC157686
0.7723	Intermediate Similarity	NPC279974
0.7723	Intermediate Similarity	NPC62407
0.7723	Intermediate Similarity	NPC259042
0.7723	Intermediate Similarity	NPC287354
0.7723	Intermediate Similarity	NPC23241
0.7723	Intermediate Similarity	NPC471624
0.7714	Intermediate Similarity	NPC122811
0.7714	Intermediate Similarity	NPC277074
0.7714	Intermediate Similarity	NPC222153
0.7714	Intermediate Similarity	NPC96217
0.7714	Intermediate Similarity	NPC282233
0.7714	Intermediate Similarity	NPC209298
0.7714	Intermediate Similarity	NPC95899
0.7714	Intermediate Similarity	NPC95585
0.7714	Intermediate Similarity	NPC275583
0.7708	Intermediate Similarity	NPC164424
0.7708	Intermediate Similarity	NPC477445
0.7706	Intermediate Similarity	NPC157476
0.77	Intermediate Similarity	NPC471902
0.77	Intermediate Similarity	NPC294263
0.77	Intermediate Similarity	NPC473690
0.77	Intermediate Similarity	NPC287118
0.7692	Intermediate Similarity	NPC75941
0.7692	Intermediate Similarity	NPC148279
0.7692	Intermediate Similarity	NPC242666
0.7692	Intermediate Similarity	NPC308824
0.7692	Intermediate Similarity	NPC236585
0.7684	Intermediate Similarity	NPC471037
0.7679	Intermediate Similarity	NPC287343
0.7679	Intermediate Similarity	NPC470854
0.7679	Intermediate Similarity	NPC97908
0.7679	Intermediate Similarity	NPC122033
0.7679	Intermediate Similarity	NPC474654
0.7677	Intermediate Similarity	NPC470378
0.7677	Intermediate Similarity	NPC232202
0.7677	Intermediate Similarity	NPC261994
0.7677	Intermediate Similarity	NPC149761
0.767	Intermediate Similarity	NPC164349
0.7658	Intermediate Similarity	NPC117712
0.7647	Intermediate Similarity	NPC472806
0.7647	Intermediate Similarity	NPC98874
0.7647	Intermediate Similarity	NPC284518
0.7647	Intermediate Similarity	NPC93245
0.7647	Intermediate Similarity	NPC327788
0.7647	Intermediate Similarity	NPC167193
0.7647	Intermediate Similarity	NPC62516
0.7647	Intermediate Similarity	NPC256227
0.7647	Intermediate Similarity	NPC157113
0.7647	Intermediate Similarity	NPC132824

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 NPC477653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	2122
0.2-0.3	3861
0.3-0.4	1889
0.4-0.5	633
0.5-0.6	227
0.6-0.7	175
0.7-0.8	13
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
0.8095	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8035	Phase 2
0.76	Intermediate Similarity	NPD8034	Phase 2
0.7573	Intermediate Similarity	NPD7902	Approved
0.7451	Intermediate Similarity	NPD7748	Approved
0.7387	Intermediate Similarity	NPD6649	Approved
0.7387	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD6373	Approved
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.7339	Intermediate Similarity	NPD5697	Approved
0.7328	Intermediate Similarity	NPD6319	Approved
0.7282	Intermediate Similarity	NPD7900	Approved
0.7282	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6899	Approved
0.7273	Intermediate Similarity	NPD6881	Approved
0.7265	Intermediate Similarity	NPD6921	Approved
0.7255	Intermediate Similarity	NPD7515	Phase 2
0.7248	Intermediate Similarity	NPD6402	Approved
0.7248	Intermediate Similarity	NPD5739	Approved
0.7248	Intermediate Similarity	NPD6675	Approved
0.7248	Intermediate Similarity	NPD7128	Approved
0.7207	Intermediate Similarity	NPD6013	Approved
0.7207	Intermediate Similarity	NPD6014	Approved
0.7207	Intermediate Similarity	NPD6012	Approved
0.7182	Intermediate Similarity	NPD5701	Approved
0.7172	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7638	Approved
0.717	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7320	Approved
0.7117	Intermediate Similarity	NPD6011	Approved
0.7105	Intermediate Similarity	NPD4632	Approved
0.7103	Intermediate Similarity	NPD7639	Approved
0.7103	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.708	Intermediate Similarity	NPD6617	Approved
0.708	Intermediate Similarity	NPD6869	Approved
0.708	Intermediate Similarity	NPD8130	Phase 1
0.708	Intermediate Similarity	NPD6847	Approved
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7049	Intermediate Similarity	NPD7736	Approved
0.7048	Intermediate Similarity	NPD5695	Phase 3
0.7034	Intermediate Similarity	NPD6054	Approved
0.7025	Intermediate Similarity	NPD6616	Approved
0.7018	Intermediate Similarity	NPD8297	Approved
0.7018	Intermediate Similarity	NPD6882	Approved
0.6991	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4634	Approved
0.6981	Remote Similarity	NPD4697	Phase 3
0.6975	Remote Similarity	NPD6016	Approved
0.6975	Remote Similarity	NPD6015	Approved
0.6967	Remote Similarity	NPD7078	Approved
0.6952	Remote Similarity	NPD5282	Discontinued
0.6944	Remote Similarity	NPD4696	Approved
0.6944	Remote Similarity	NPD5285	Approved
0.6944	Remote Similarity	NPD5286	Approved
0.6937	Remote Similarity	NPD6008	Approved
0.6931	Remote Similarity	NPD3618	Phase 1
0.6923	Remote Similarity	NPD7115	Discovery
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.6923	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6370	Approved
0.6917	Remote Similarity	NPD5988	Approved
0.6916	Remote Similarity	NPD4755	Approved
0.6903	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6059	Approved
0.6863	Remote Similarity	NPD3573	Approved
0.6833	Remote Similarity	NPD5983	Phase 2
0.6829	Remote Similarity	NPD8293	Discontinued
0.6822	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5221	Approved
0.6822	Remote Similarity	NPD5222	Approved
0.6818	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD5226	Approved
0.6818	Remote Similarity	NPD5211	Phase 2
0.6818	Remote Similarity	NPD4633	Approved
0.6818	Remote Similarity	NPD5224	Approved
0.6804	Remote Similarity	NPD6697	Approved
0.6804	Remote Similarity	NPD6118	Approved
0.6804	Remote Similarity	NPD6115	Approved
0.6804	Remote Similarity	NPD6114	Approved
0.6796	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD6672	Approved
0.6789	Remote Similarity	NPD4700	Approved
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5173	Approved
0.6757	Remote Similarity	NPD5174	Approved
0.6757	Remote Similarity	NPD5175	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4753	Phase 2
0.6731	Remote Similarity	NPD6101	Approved
0.6729	Remote Similarity	NPD5210	Approved
0.6729	Remote Similarity	NPD4629	Approved
0.6727	Remote Similarity	NPD5223	Approved
0.6726	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7604	Phase 2
0.67	Remote Similarity	NPD3667	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6697	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6695	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6639	Remote Similarity	NPD6317	Approved
0.6635	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6336	Discontinued
0.6604	Remote Similarity	NPD6079	Approved
0.6604	Remote Similarity	NPD7637	Suspended
0.6602	Remote Similarity	NPD7334	Approved
0.6602	Remote Similarity	NPD6409	Approved
0.6602	Remote Similarity	NPD7521	Approved
0.6602	Remote Similarity	NPD5330	Approved
0.6602	Remote Similarity	NPD7146	Approved
0.6602	Remote Similarity	NPD6684	Approved
0.6602	Remote Similarity	NPD6098	Approved
0.6598	Remote Similarity	NPD6117	Approved
0.6587	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD6335	Approved
0.6583	Remote Similarity	NPD6314	Approved
0.6583	Remote Similarity	NPD6313	Approved
0.6574	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6904	Approved
0.6571	Remote Similarity	NPD6080	Approved
0.6571	Remote Similarity	NPD5328	Approved
0.6571	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6673	Approved
0.6569	Remote Similarity	NPD4786	Approved
0.6557	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6868	Approved
0.6542	Remote Similarity	NPD4202	Approved
0.6531	Remote Similarity	NPD6116	Phase 1
0.6522	Remote Similarity	NPD4729	Approved
0.6522	Remote Similarity	NPD4730	Approved
0.6518	Remote Similarity	NPD7632	Discontinued
0.65	Remote Similarity	NPD4695	Discontinued
0.6495	Remote Similarity	NPD3703	Phase 2
0.6491	Remote Similarity	NPD4767	Approved
0.6491	Remote Similarity	NPD4768	Approved
0.6476	Remote Similarity	NPD6903	Approved
0.6471	Remote Similarity	NPD4788	Approved
0.646	Remote Similarity	NPD4754	Approved
0.6449	Remote Similarity	NPD5281	Approved
0.6449	Remote Similarity	NPD5284	Approved
0.6449	Remote Similarity	NPD5694	Approved
0.6449	Remote Similarity	NPD5693	Phase 1
0.6435	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD1700	Approved
0.6423	Remote Similarity	NPD6908	Approved
0.6423	Remote Similarity	NPD6909	Approved
0.641	Remote Similarity	NPD5247	Approved
0.641	Remote Similarity	NPD5249	Phase 3
0.641	Remote Similarity	NPD5250	Approved
0.641	Remote Similarity	NPD5251	Approved
0.641	Remote Similarity	NPD5248	Approved
0.6408	Remote Similarity	NPD3665	Phase 1
0.6408	Remote Similarity	NPD3133	Approved
0.6408	Remote Similarity	NPD3668	Phase 3
0.6408	Remote Similarity	NPD3666	Approved
0.6408	Remote Similarity	NPD4197	Approved
0.64	Remote Similarity	NPD7645	Phase 2
0.6392	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5128	Approved
0.6379	Remote Similarity	NPD6686	Approved
0.6378	Remote Similarity	NPD6033	Approved
0.6356	Remote Similarity	NPD5215	Approved
0.6356	Remote Similarity	NPD5216	Approved
0.6356	Remote Similarity	NPD5217	Approved
0.6355	Remote Similarity	NPD5692	Phase 3
0.6349	Remote Similarity	NPD7507	Approved
0.6346	Remote Similarity	NPD1694	Approved
0.6346	Remote Similarity	NPD5329	Approved
0.6337	Remote Similarity	NPD7525	Registered
0.633	Remote Similarity	NPD6001	Approved
0.6316	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6050	Approved
0.6286	Remote Similarity	NPD5690	Phase 2
0.6286	Remote Similarity	NPD5279	Phase 3
0.6275	Remote Similarity	NPD5369	Approved
0.6271	Remote Similarity	NPD5169	Approved
0.6271	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5135	Approved
0.6239	Remote Similarity	NPD5168	Approved
0.6218	Remote Similarity	NPD5127	Approved
0.6214	Remote Similarity	NPD4221	Approved
0.6214	Remote Similarity	NPD4223	Phase 3
0.6214	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5207	Approved
0.6194	Remote Similarity	NPD6334	Approved
0.6194	Remote Similarity	NPD6333	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