NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	310.18
Volume:	315.597
LogP:	2.713
LogD:	1.861
LogS:	-4.198
# Rotatable Bonds:	0
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	6.129
Fsp3:	0.882
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.182
MDCK Permeability:	8.0705969594419e-05
Pgp-inhibitor:	0.423
Pgp-substrate:	0.286
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.609

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.708
Plasma Protein Binding (PPB):	52.18048858642578%
Volume Distribution (VD):	1.265
Pgp-substrate:	40.514591217041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.384

ADMET: Excretion

Clearance (CL):	9.175
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.75
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.625
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.198
Carcinogencity:	0.517
Eye Corrosion:	0.95
Eye Irritation:	0.509
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC477205

Natural Product ID:	NPC477205
*Common Name:**	Portentol
IUPAC Name:	(1R,3'R,4S,4'R,5'S,6R,6'R,7S,8R)-4'-hydroxy-3',4,5',6,6',7-hexamethylspiro[2-oxabicyclo[2.2.2]octane-8,2'-oxane]-3,5-dione
Synonyms:	Portentol
Standard InCHIKey:	CVPVGRDVSAJUQS-QKOFGJBMSA-N
Standard InCHI:	InChI=1S/C17H26O5/c1-7-11(5)22-17(9(3)12(7)18)10(4)13-8(2)14(19)16(17,6)15(20)21-13/h7-13,18H,1-6H3/t7-,8-,9-,10+,11-,12-,13+,16+,17-/m1/s1
SMILES:	C[C@@H]1[C@H](O[C@]2([C@@H]([C@@H]1O)C)[C@H]([C@@H]3[C@H](C(=O)[C@]2(C(=O)O3)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO13075	Gustavia hexapetala	Species	Lecythidaceae	Eukaryota	n.a.	Peru	1979	PMID[15217278]
NPO13075	Gustavia hexapetala	Species	Lecythidaceae	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
GI50	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI50	>	10	ug/ml	PMID[15217278]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	7	ug/ml	PMID[15217278]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10	ug/ml	PMID[15217278]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	4.7	ug/ml	PMID[15217278]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	4.7	ug/ml	PMID[15217278]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	>	10	ug/ml	PMID[15217278]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	1.3	ug/ml	PMID[15217278]

☑ 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 NPC477205 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	499
0.1-0.2	3342
0.2-0.3	7886
0.3-0.4	13979
0.4-0.5	7430
0.5-0.6	5062
0.6-0.7	3380
0.7-0.8	1057
0.8-0.85	43
0.85-0.9	10
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC83242
0.8916	High Similarity	NPC477434
0.869	High Similarity	NPC237938
0.869	High Similarity	NPC219535
0.8588	High Similarity	NPC473350
0.8409	Intermediate Similarity	NPC477440
0.8409	Intermediate Similarity	NPC477443
0.8409	Intermediate Similarity	NPC200580
0.8395	Intermediate Similarity	NPC474020
0.8315	Intermediate Similarity	NPC88337
0.8315	Intermediate Similarity	NPC477444
0.8315	Intermediate Similarity	NPC477442
0.8315	Intermediate Similarity	NPC477433
0.8315	Intermediate Similarity	NPC475211
0.8295	Intermediate Similarity	NPC131104
0.8295	Intermediate Similarity	NPC473319
0.8295	Intermediate Similarity	NPC3032
0.8261	Intermediate Similarity	NPC193785
0.8256	Intermediate Similarity	NPC473336
0.8256	Intermediate Similarity	NPC471044
0.8211	Intermediate Similarity	NPC471254
0.8202	Intermediate Similarity	NPC67653
0.8202	Intermediate Similarity	NPC61688
0.8202	Intermediate Similarity	NPC471459
0.8182	Intermediate Similarity	NPC470920
0.8161	Intermediate Similarity	NPC477445
0.8152	Intermediate Similarity	NPC62407
0.8152	Intermediate Similarity	NPC287354
0.814	Intermediate Similarity	NPC15091
0.8132	Intermediate Similarity	NPC476189
0.809	Intermediate Similarity	NPC236459
0.809	Intermediate Similarity	NPC476435
0.809	Intermediate Similarity	NPC477614
0.809	Intermediate Similarity	NPC226491
0.8068	Intermediate Similarity	NPC302111
0.8068	Intermediate Similarity	NPC120395
0.8068	Intermediate Similarity	NPC248216
0.8046	Intermediate Similarity	NPC50438
0.8046	Intermediate Similarity	NPC475689
0.8041	Intermediate Similarity	NPC88469
0.8	Intermediate Similarity	NPC125366
0.8	Intermediate Similarity	NPC56962
0.8	Intermediate Similarity	NPC24705
0.7938	Intermediate Similarity	NPC471253
0.7931	Intermediate Similarity	NPC227170
0.7917	Intermediate Similarity	NPC236585
0.7907	Intermediate Similarity	NPC476071
0.7907	Intermediate Similarity	NPC475743
0.7895	Intermediate Similarity	NPC474793
0.7889	Intermediate Similarity	NPC476379
0.7889	Intermediate Similarity	NPC471221
0.7872	Intermediate Similarity	NPC163685
0.7865	Intermediate Similarity	NPC477441
0.7865	Intermediate Similarity	NPC476717
0.7865	Intermediate Similarity	NPC475729
0.7865	Intermediate Similarity	NPC474215
0.7849	Intermediate Similarity	NPC309127
0.7849	Intermediate Similarity	NPC247877
0.7841	Intermediate Similarity	NPC181871
0.7841	Intermediate Similarity	NPC473299
0.7841	Intermediate Similarity	NPC9060
0.7835	Intermediate Similarity	NPC470172
0.7826	Intermediate Similarity	NPC476934
0.7778	Intermediate Similarity	NPC263802
0.7766	Intermediate Similarity	NPC217329
0.7766	Intermediate Similarity	NPC82633
0.7766	Intermediate Similarity	NPC470232
0.7765	Intermediate Similarity	NPC475725
0.7755	Intermediate Similarity	NPC96217
0.7755	Intermediate Similarity	NPC473406
0.7753	Intermediate Similarity	NPC474572
0.7753	Intermediate Similarity	NPC131350
0.7742	Intermediate Similarity	NPC474379
0.7732	Intermediate Similarity	NPC46848
0.7732	Intermediate Similarity	NPC148279
0.7723	Intermediate Similarity	NPC469983
0.7717	Intermediate Similarity	NPC77756
0.7711	Intermediate Similarity	NPC55508
0.7708	Intermediate Similarity	NPC253995
0.7701	Intermediate Similarity	NPC329490
0.7701	Intermediate Similarity	NPC328639
0.77	Intermediate Similarity	NPC61071
0.7692	Intermediate Similarity	NPC90676
0.7684	Intermediate Similarity	NPC329910
0.7684	Intermediate Similarity	NPC116683
0.7684	Intermediate Similarity	NPC235109
0.7684	Intermediate Similarity	NPC477264
0.7677	Intermediate Similarity	NPC474558
0.7677	Intermediate Similarity	NPC202793
0.7674	Intermediate Similarity	NPC320144
0.7674	Intermediate Similarity	NPC275243
0.7674	Intermediate Similarity	NPC80891
0.7674	Intermediate Similarity	NPC201276
0.766	Intermediate Similarity	NPC469982
0.766	Intermediate Similarity	NPC470386
0.766	Intermediate Similarity	NPC475118
0.766	Intermediate Similarity	NPC470385
0.7653	Intermediate Similarity	NPC304832
0.7653	Intermediate Similarity	NPC88203
0.7653	Intermediate Similarity	NPC286519
0.7653	Intermediate Similarity	NPC275990
0.7653	Intermediate Similarity	NPC76866
0.7653	Intermediate Similarity	NPC148628
0.7653	Intermediate Similarity	NPC214946
0.7653	Intermediate Similarity	NPC246736
0.7647	Intermediate Similarity	NPC474003
0.7647	Intermediate Similarity	NPC307865
0.764	Intermediate Similarity	NPC319909
0.7634	Intermediate Similarity	NPC52756
0.7634	Intermediate Similarity	NPC216137
0.7634	Intermediate Similarity	NPC475878
0.7629	Intermediate Similarity	NPC267921
0.7629	Intermediate Similarity	NPC94906
0.7624	Intermediate Similarity	NPC208461
0.7624	Intermediate Similarity	NPC232133
0.7624	Intermediate Similarity	NPC289702
0.7619	Intermediate Similarity	NPC159789
0.7614	Intermediate Similarity	NPC61107
0.7614	Intermediate Similarity	NPC289486
0.7609	Intermediate Similarity	NPC59682
0.7586	Intermediate Similarity	NPC134227
0.7586	Intermediate Similarity	NPC477851
0.7579	Intermediate Similarity	NPC17336
0.7579	Intermediate Similarity	NPC470229
0.7576	Intermediate Similarity	NPC139347
0.7558	Intermediate Similarity	NPC171426
0.7558	Intermediate Similarity	NPC34046
0.7558	Intermediate Similarity	NPC324700
0.7558	Intermediate Similarity	NPC185465
0.7558	Intermediate Similarity	NPC224802
0.7558	Intermediate Similarity	NPC80089
0.7556	Intermediate Similarity	NPC476715
0.7551	Intermediate Similarity	NPC14634
0.7551	Intermediate Similarity	NPC163963
0.7551	Intermediate Similarity	NPC289148
0.7551	Intermediate Similarity	NPC298266
0.7551	Intermediate Similarity	NPC259654
0.7551	Intermediate Similarity	NPC52899
0.7528	Intermediate Similarity	NPC476721
0.7527	Intermediate Similarity	NPC470114
0.7527	Intermediate Similarity	NPC185529
0.7527	Intermediate Similarity	NPC472146
0.7526	Intermediate Similarity	NPC98837
0.7526	Intermediate Similarity	NPC162459
0.7526	Intermediate Similarity	NPC38296
0.7526	Intermediate Similarity	NPC89099
0.7526	Intermediate Similarity	NPC20479
0.7526	Intermediate Similarity	NPC472028
0.7526	Intermediate Similarity	NPC38471
0.7526	Intermediate Similarity	NPC26270
0.7526	Intermediate Similarity	NPC28864
0.7526	Intermediate Similarity	NPC474724
0.7526	Intermediate Similarity	NPC477653
0.7526	Intermediate Similarity	NPC472144
0.7526	Intermediate Similarity	NPC471038
0.7525	Intermediate Similarity	NPC96333
0.7525	Intermediate Similarity	NPC88833
0.75	Intermediate Similarity	NPC470387
0.75	Intermediate Similarity	NPC254123
0.75	Intermediate Similarity	NPC101842
0.75	Intermediate Similarity	NPC84928
0.75	Intermediate Similarity	NPC476964
0.7476	Intermediate Similarity	NPC470622
0.7476	Intermediate Similarity	NPC85391
0.7475	Intermediate Similarity	NPC124544
0.7474	Intermediate Similarity	NPC47853
0.7474	Intermediate Similarity	NPC470424
0.7473	Intermediate Similarity	NPC472272
0.7473	Intermediate Similarity	NPC80700
0.747	Intermediate Similarity	NPC478227
0.7451	Intermediate Similarity	NPC473410
0.7451	Intermediate Similarity	NPC471094
0.7451	Intermediate Similarity	NPC469826
0.7451	Intermediate Similarity	NPC469984
0.7449	Intermediate Similarity	NPC287676
0.7449	Intermediate Similarity	NPC472972
0.7449	Intermediate Similarity	NPC37047
0.7449	Intermediate Similarity	NPC293890
0.7449	Intermediate Similarity	NPC293866
0.7449	Intermediate Similarity	NPC180733
0.7449	Intermediate Similarity	NPC41971
0.7447	Intermediate Similarity	NPC198242
0.7447	Intermediate Similarity	NPC211403
0.7444	Intermediate Similarity	NPC34984
0.7444	Intermediate Similarity	NPC65133
0.7444	Intermediate Similarity	NPC25037
0.7442	Intermediate Similarity	NPC477918
0.7442	Intermediate Similarity	NPC471151
0.7442	Intermediate Similarity	NPC112463
0.7442	Intermediate Similarity	NPC143250
0.7426	Intermediate Similarity	NPC138908
0.7426	Intermediate Similarity	NPC295366
0.7426	Intermediate Similarity	NPC200957
0.7426	Intermediate Similarity	NPC37600
0.7423	Intermediate Similarity	NPC472145
0.7423	Intermediate Similarity	NPC10864
0.7423	Intermediate Similarity	NPC471241
0.7423	Intermediate Similarity	NPC96839
0.7423	Intermediate Similarity	NPC472273
0.7423	Intermediate Similarity	NPC111187

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 NPC477205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	554
0.1-0.2	3527
0.2-0.3	3217
0.3-0.4	1164
0.4-0.5	362
0.5-0.6	225
0.6-0.7	84
0.7-0.8	17
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
0.7624	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3703	Phase 2
0.7558	Intermediate Similarity	NPD6118	Approved
0.7558	Intermediate Similarity	NPD6115	Approved
0.7558	Intermediate Similarity	NPD6114	Approved
0.7558	Intermediate Similarity	NPD6697	Approved
0.7326	Intermediate Similarity	NPD6117	Approved
0.7241	Intermediate Similarity	NPD6116	Phase 1
0.7209	Intermediate Similarity	NPD3702	Approved
0.7093	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1700	Approved
0.7024	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1780	Approved
0.6923	Remote Similarity	NPD1779	Approved
0.686	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6921	Approved
0.6774	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3669	Approved
0.6757	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6628	Remote Similarity	NPD3698	Phase 2
0.6604	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.6579	Remote Similarity	NPD6319	Approved
0.6574	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4245	Approved
0.6552	Remote Similarity	NPD4244	Approved
0.6552	Remote Similarity	NPD8328	Phase 3
0.6548	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5701	Approved
0.6542	Remote Similarity	NPD5697	Approved
0.6531	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6101	Approved
0.6512	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5360	Phase 3
0.6481	Remote Similarity	NPD6899	Approved
0.6481	Remote Similarity	NPD6881	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6477	Remote Similarity	NPD6081	Approved
0.6458	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7748	Approved
0.6429	Remote Similarity	NPD371	Approved
0.6422	Remote Similarity	NPD6012	Approved
0.6422	Remote Similarity	NPD6013	Approved
0.6422	Remote Similarity	NPD6372	Approved
0.6422	Remote Similarity	NPD6373	Approved
0.6422	Remote Similarity	NPD6014	Approved
0.6413	Remote Similarity	NPD4238	Approved
0.6413	Remote Similarity	NPD3671	Phase 1
0.6413	Remote Similarity	NPD4802	Phase 2
0.64	Remote Similarity	NPD8034	Phase 2
0.64	Remote Similarity	NPD7515	Phase 2
0.64	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD4789	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6356	Remote Similarity	NPD7492	Approved
0.6346	Remote Similarity	NPD7638	Approved
0.6339	Remote Similarity	NPD4632	Approved
0.6339	Remote Similarity	NPD8133	Approved
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6333	Remote Similarity	NPD1811	Approved
0.6333	Remote Similarity	NPD1810	Approved
0.633	Remote Similarity	NPD6011	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6306	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD8130	Phase 1
0.6306	Remote Similarity	NPD6617	Approved
0.6306	Remote Similarity	NPD6847	Approved
0.6306	Remote Similarity	NPD6649	Approved
0.6306	Remote Similarity	NPD6869	Approved
0.6303	Remote Similarity	NPD6616	Approved
0.6296	Remote Similarity	NPD6008	Approved
0.6293	Remote Similarity	NPD6054	Approved
0.6293	Remote Similarity	NPD6059	Approved
0.6292	Remote Similarity	NPD4758	Discontinued
0.6286	Remote Similarity	NPD7640	Approved
0.6286	Remote Similarity	NPD7639	Approved
0.6281	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD7902	Approved
0.625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD6016	Approved
0.6239	Remote Similarity	NPD6015	Approved
0.6216	Remote Similarity	NPD4634	Approved
0.62	Remote Similarity	NPD5328	Approved
0.6198	Remote Similarity	NPD7736	Approved
0.6186	Remote Similarity	NPD6370	Approved
0.6186	Remote Similarity	NPD5988	Approved
0.6176	Remote Similarity	NPD6399	Phase 3
0.6174	Remote Similarity	NPD6009	Approved
0.6168	Remote Similarity	NPD8138	Approved
0.6168	Remote Similarity	NPD8086	Approved
0.6168	Remote Similarity	NPD8082	Approved
0.6168	Remote Similarity	NPD8139	Approved
0.6168	Remote Similarity	NPD7632	Discontinued
0.6168	Remote Similarity	NPD8085	Approved
0.6168	Remote Similarity	NPD8084	Approved
0.6168	Remote Similarity	NPD8083	Approved
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD229	Approved
0.6132	Remote Similarity	NPD4696	Approved
0.6132	Remote Similarity	NPD5285	Approved
0.6132	Remote Similarity	NPD5286	Approved
0.6132	Remote Similarity	NPD8418	Phase 2
0.6132	Remote Similarity	NPD4700	Approved
0.6125	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8275	Approved
0.6111	Remote Similarity	NPD8276	Approved
0.6105	Remote Similarity	NPD6928	Phase 2
0.6102	Remote Similarity	NPD5983	Phase 2
0.6095	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD6083	Phase 2
0.6091	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6274	Approved
0.6078	Remote Similarity	NPD6079	Approved
0.6064	Remote Similarity	NPD5364	Discontinued
0.6061	Remote Similarity	NPD3618	Phase 1
0.6058	Remote Similarity	NPD5695	Phase 3
0.6055	Remote Similarity	NPD8081	Approved
0.6047	Remote Similarity	NPD7909	Approved
0.6034	Remote Similarity	NPD7115	Discovery
0.6033	Remote Similarity	NPD7507	Approved
0.6019	Remote Similarity	NPD5225	Approved
0.6019	Remote Similarity	NPD5226	Approved
0.6019	Remote Similarity	NPD4633	Approved
0.6019	Remote Similarity	NPD5224	Approved
0.6019	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD2686	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD2687	Approved
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2254	Approved
0.6	Remote Similarity	NPD8393	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD3667	Approved
0.5979	Remote Similarity	NPD7345	Approved
0.5963	Remote Similarity	NPD5175	Approved
0.5963	Remote Similarity	NPD5174	Approved
0.5962	Remote Similarity	NPD7900	Approved
0.5962	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6940	Discontinued
0.5946	Remote Similarity	NPD6412	Phase 2
0.5943	Remote Similarity	NPD5173	Approved
0.5932	Remote Similarity	NPD7100	Approved
0.5932	Remote Similarity	NPD7101	Approved
0.5926	Remote Similarity	NPD5223	Approved
0.5926	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5141	Approved
0.5902	Remote Similarity	NPD6336	Discontinued
0.59	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6317	Approved
0.5893	Remote Similarity	NPD6686	Approved
0.5888	Remote Similarity	NPD4225	Approved
0.5888	Remote Similarity	NPD5696	Approved
0.5865	Remote Similarity	NPD8171	Discontinued
0.5865	Remote Similarity	NPD4202	Approved
0.5859	Remote Similarity	NPD4786	Approved
0.5856	Remote Similarity	NPD4767	Approved
0.5856	Remote Similarity	NPD4768	Approved
0.5847	Remote Similarity	NPD6335	Approved
0.5847	Remote Similarity	NPD6313	Approved
0.5847	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD8513	Phase 3
0.5833	Remote Similarity	NPD6909	Approved
0.5833	Remote Similarity	NPD8515	Approved
0.5833	Remote Similarity	NPD8516	Approved
0.5833	Remote Similarity	NPD6908	Approved
0.5833	Remote Similarity	NPD8517	Approved
0.5818	Remote Similarity	NPD4754	Approved
0.5812	Remote Similarity	NPD6868	Approved
0.581	Remote Similarity	NPD5282	Discontinued
0.5806	Remote Similarity	NPD6033	Approved
0.5804	Remote Similarity	NPD8307	Discontinued
0.5804	Remote Similarity	NPD8140	Approved
0.5795	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7637	Suspended
0.5766	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3198	Approved
0.5758	Remote Similarity	NPD4788	Approved
0.5752	Remote Similarity	NPD4730	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