NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	660.42
Volume:	691.588
LogP:	5.854
LogD:	4.396
LogS:	-4.945
# Rotatable Bonds:	10
TPSA:	114.43
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	5.431
Fsp3:	0.895
Lipinski Rule-of-5:	Rejected
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:	-4.925
MDCK Permeability:	4.626521695172414e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.262
30% Bioavailability (F30%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	78.50382995605469%
Volume Distribution (VD):	1.548
Pgp-substrate:	14.167838096618652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.121
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.278
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	3.43
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.421
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.468
Skin Sensitization:	0.956
Carcinogencity:	0.025
Eye Corrosion:	0.33
Eye Irritation:	0.112
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC477284

Natural Product ID:	NPC477284
*Common Name:**	(20S,24R)-1beta,3alpha,12beta,25-Tetraacetoxy-20,24-epoxydammarane
IUPAC Name:	[(1R,3R,5S,8R,9S,10R,12R,13R,14R,17S)-1,3-diacetyloxy-17-[(2S,5R)-5-(2-acetyloxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
Synonyms:
Standard InCHIKey:	CSLSINMBGVKCNB-UXSFOGSZSA-N
Standard InCHI:	InChI=1S/C38H60O9/c1-21(39)43-26-19-28-35(9,17-14-27-33(5,6)30(44-22(2)40)20-31(38(27,28)12)45-23(3)41)36(10)16-13-25(32(26)36)37(11)18-15-29(47-37)34(7,8)46-24(4)42/h25-32H,13-20H2,1-12H3/t25-,26+,27-,28-,29+,30+,31+,32-,35+,36+,37-,38-/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2[C@@](CC[C@@H]3[C@@]2([C@@H](C[C@H](C3(C)C)OC(=O)C)OC(=O)C)C)([C@]4([C@H]1[C@H](CC4)[C@@]5(CC[C@@H](O5)C(C)(C)OC(=O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10372203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO22221	Ibicella lutea	Species	Martyniaceae	Eukaryota	n.a.	El Volcan, Dpto. La Capital, Province of San Luis, Argentina	2001-MAR	PMID[14695802]
NPO22221	Ibicella lutea	Species	Martyniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	5	ug/ml	PMID[14695802]

☑ 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 NPC477284 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	471
0.1-0.2	4370
0.2-0.3	12702
0.3-0.4	11216
0.4-0.5	5345
0.5-0.6	5296
0.6-0.7	2622
0.7-0.8	616
0.8-0.85	42
0.85-0.9	10
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC477287
0.95	High Similarity	NPC477283
0.9259	High Similarity	NPC215968
0.9259	High Similarity	NPC155531
0.9	High Similarity	NPC286719
0.9	High Similarity	NPC477286
0.8889	High Similarity	NPC477285
0.8889	High Similarity	NPC111582
0.8875	High Similarity	NPC190940
0.881	High Similarity	NPC201607
0.881	High Similarity	NPC56777
0.8721	High Similarity	NPC473066
0.8571	High Similarity	NPC103782
0.8571	High Similarity	NPC114378
0.8537	High Similarity	NPC60018
0.8537	High Similarity	NPC202688
0.8537	High Similarity	NPC154043
0.8452	Intermediate Similarity	NPC266651
0.8415	Intermediate Similarity	NPC470154
0.8415	Intermediate Similarity	NPC73515
0.8395	Intermediate Similarity	NPC476176
0.8395	Intermediate Similarity	NPC477282
0.8395	Intermediate Similarity	NPC81074
0.8375	Intermediate Similarity	NPC212453
0.8333	Intermediate Similarity	NPC237071
0.8333	Intermediate Similarity	NPC203434
0.8333	Intermediate Similarity	NPC145553
0.8333	Intermediate Similarity	NPC238796
0.8313	Intermediate Similarity	NPC470155
0.8313	Intermediate Similarity	NPC477447
0.8313	Intermediate Similarity	NPC477446
0.8293	Intermediate Similarity	NPC471217
0.8293	Intermediate Similarity	NPC471216
0.8293	Intermediate Similarity	NPC474714
0.8202	Intermediate Similarity	NPC256104
0.8202	Intermediate Similarity	NPC122083
0.8202	Intermediate Similarity	NPC182740
0.8202	Intermediate Similarity	NPC211845
0.8202	Intermediate Similarity	NPC35164
0.8193	Intermediate Similarity	NPC71541
0.8193	Intermediate Similarity	NPC470156
0.8182	Intermediate Similarity	NPC470114
0.8172	Intermediate Similarity	NPC475574
0.8171	Intermediate Similarity	NPC220379
0.8152	Intermediate Similarity	NPC292775
0.8148	Intermediate Similarity	NPC64081
0.8148	Intermediate Similarity	NPC133596
0.8148	Intermediate Similarity	NPC11907
0.8148	Intermediate Similarity	NPC474574
0.814	Intermediate Similarity	NPC131365
0.8132	Intermediate Similarity	NPC156377
0.8132	Intermediate Similarity	NPC116683
0.8125	Intermediate Similarity	NPC478105
0.8111	Intermediate Similarity	NPC191915
0.8111	Intermediate Similarity	NPC151214
0.8101	Intermediate Similarity	NPC123122
0.8072	Intermediate Similarity	NPC472951
0.8072	Intermediate Similarity	NPC472943
0.8072	Intermediate Similarity	NPC475456
0.8068	Intermediate Similarity	NPC82955
0.8049	Intermediate Similarity	NPC471045
0.8046	Intermediate Similarity	NPC5943
0.8022	Intermediate Similarity	NPC94582
0.8022	Intermediate Similarity	NPC57964
0.8022	Intermediate Similarity	NPC21897
0.8	Intermediate Similarity	NPC167644
0.8	Intermediate Similarity	NPC272359
0.8	Intermediate Similarity	NPC311246
0.7979	Intermediate Similarity	NPC472081
0.7979	Intermediate Similarity	NPC476512
0.7979	Intermediate Similarity	NPC108227
0.7935	Intermediate Similarity	NPC296936
0.7935	Intermediate Similarity	NPC252056
0.7931	Intermediate Similarity	NPC474008
0.7912	Intermediate Similarity	NPC477495
0.7912	Intermediate Similarity	NPC477224
0.7912	Intermediate Similarity	NPC3538
0.7912	Intermediate Similarity	NPC113500
0.7907	Intermediate Similarity	NPC18953
0.7907	Intermediate Similarity	NPC320824
0.7907	Intermediate Similarity	NPC65133
0.7901	Intermediate Similarity	NPC91387
0.7901	Intermediate Similarity	NPC270306
0.7901	Intermediate Similarity	NPC186851
0.7901	Intermediate Similarity	NPC231680
0.7895	Intermediate Similarity	NPC134967
0.7895	Intermediate Similarity	NPC114700
0.7895	Intermediate Similarity	NPC470029
0.7895	Intermediate Similarity	NPC310138
0.7889	Intermediate Similarity	NPC210759
0.7889	Intermediate Similarity	NPC229801
0.7889	Intermediate Similarity	NPC219516
0.7889	Intermediate Similarity	NPC307167
0.7882	Intermediate Similarity	NPC475388
0.7882	Intermediate Similarity	NPC13494
0.7882	Intermediate Similarity	NPC470611
0.7875	Intermediate Similarity	NPC476718
0.7872	Intermediate Similarity	NPC470030
0.7865	Intermediate Similarity	NPC20822
0.7857	Intermediate Similarity	NPC16449
0.7841	Intermediate Similarity	NPC43912
0.7841	Intermediate Similarity	NPC45833
0.7841	Intermediate Similarity	NPC210658
0.7841	Intermediate Similarity	NPC213658
0.7841	Intermediate Similarity	NPC140446
0.7841	Intermediate Similarity	NPC161928
0.7841	Intermediate Similarity	NPC110365
0.7841	Intermediate Similarity	NPC62202
0.7831	Intermediate Similarity	NPC43463
0.7812	Intermediate Similarity	NPC476837
0.7812	Intermediate Similarity	NPC97260
0.7812	Intermediate Similarity	NPC139181
0.7791	Intermediate Similarity	NPC473742
0.7791	Intermediate Similarity	NPC69953
0.7791	Intermediate Similarity	NPC470070
0.7778	Intermediate Similarity	NPC472945
0.7778	Intermediate Similarity	NPC472944
0.7778	Intermediate Similarity	NPC473542
0.7778	Intermediate Similarity	NPC10274
0.7778	Intermediate Similarity	NPC279329
0.7765	Intermediate Similarity	NPC476494
0.7765	Intermediate Similarity	NPC119922
0.7765	Intermediate Similarity	NPC116320
0.7753	Intermediate Similarity	NPC128475
0.7753	Intermediate Similarity	NPC470872
0.775	Intermediate Similarity	NPC252182
0.775	Intermediate Similarity	NPC470071
0.775	Intermediate Similarity	NPC1340
0.775	Intermediate Similarity	NPC187471
0.7727	Intermediate Similarity	NPC64862
0.7727	Intermediate Similarity	NPC471411
0.7727	Intermediate Similarity	NPC471410
0.7717	Intermediate Similarity	NPC45959
0.7717	Intermediate Similarity	NPC24960
0.7717	Intermediate Similarity	NPC305418
0.7717	Intermediate Similarity	NPC252253
0.7717	Intermediate Similarity	NPC473774
0.7717	Intermediate Similarity	NPC175
0.7711	Intermediate Similarity	NPC171658
0.7692	Intermediate Similarity	NPC5632
0.7692	Intermediate Similarity	NPC36372
0.7692	Intermediate Similarity	NPC293609
0.7692	Intermediate Similarity	NPC149966
0.7683	Intermediate Similarity	NPC158208
0.7683	Intermediate Similarity	NPC196136
0.7683	Intermediate Similarity	NPC243027
0.7677	Intermediate Similarity	NPC473517
0.7674	Intermediate Similarity	NPC208912
0.7674	Intermediate Similarity	NPC242771
0.7674	Intermediate Similarity	NPC100366
0.7674	Intermediate Similarity	NPC164289
0.7674	Intermediate Similarity	NPC2096
0.7674	Intermediate Similarity	NPC311642
0.7667	Intermediate Similarity	NPC131466
0.766	Intermediate Similarity	NPC477223
0.766	Intermediate Similarity	NPC477222
0.766	Intermediate Similarity	NPC470591
0.7653	Intermediate Similarity	NPC306776
0.7647	Intermediate Similarity	NPC186594
0.7634	Intermediate Similarity	NPC473065
0.7634	Intermediate Similarity	NPC473067
0.7634	Intermediate Similarity	NPC241047
0.7634	Intermediate Similarity	NPC473064
0.7619	Intermediate Similarity	NPC471769
0.7614	Intermediate Similarity	NPC235402
0.7614	Intermediate Similarity	NPC290612
0.7609	Intermediate Similarity	NPC88962
0.7609	Intermediate Similarity	NPC277774
0.7609	Intermediate Similarity	NPC475307
0.7609	Intermediate Similarity	NPC144790
0.7609	Intermediate Similarity	NPC149400
0.7604	Intermediate Similarity	NPC476838
0.7604	Intermediate Similarity	NPC476839
0.759	Intermediate Similarity	NPC136424
0.7586	Intermediate Similarity	NPC475820
0.7586	Intermediate Similarity	NPC213737
0.7586	Intermediate Similarity	NPC474284
0.7586	Intermediate Similarity	NPC29342
0.7586	Intermediate Similarity	NPC474253
0.7586	Intermediate Similarity	NPC474346
0.7586	Intermediate Similarity	NPC2572
0.7579	Intermediate Similarity	NPC473638
0.7561	Intermediate Similarity	NPC192501
0.7561	Intermediate Similarity	NPC304499
0.7561	Intermediate Similarity	NPC10476
0.7561	Intermediate Similarity	NPC55508
0.7561	Intermediate Similarity	NPC228994
0.7558	Intermediate Similarity	NPC58631
0.7558	Intermediate Similarity	NPC211049
0.7556	Intermediate Similarity	NPC281004
0.7556	Intermediate Similarity	NPC221993
0.7556	Intermediate Similarity	NPC476379
0.7556	Intermediate Similarity	NPC476435
0.7556	Intermediate Similarity	NPC473436
0.7556	Intermediate Similarity	NPC471221
0.7553	Intermediate Similarity	NPC111834
0.7553	Intermediate Similarity	NPC304011
0.7553	Intermediate Similarity	NPC306797
0.7553	Intermediate Similarity	NPC169270
0.7553	Intermediate Similarity	NPC475178

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 NPC477284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	4281
0.2-0.3	3103
0.3-0.4	750
0.4-0.5	283
0.5-0.6	215
0.6-0.7	65
0.7-0.8	10
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
0.7419	Intermediate Similarity	NPD8171	Discontinued
0.7412	Intermediate Similarity	NPD6118	Approved
0.7412	Intermediate Similarity	NPD6114	Approved
0.7412	Intermediate Similarity	NPD6115	Approved
0.7412	Intermediate Similarity	NPD6697	Approved
0.7294	Intermediate Similarity	NPD6116	Phase 1
0.7284	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6928	Phase 2
0.7176	Intermediate Similarity	NPD6117	Approved
0.703	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5777	Approved
0.6771	Remote Similarity	NPD8035	Phase 2
0.6771	Remote Similarity	NPD8034	Phase 2
0.6733	Remote Similarity	NPD1700	Approved
0.6727	Remote Similarity	NPD7327	Approved
0.6727	Remote Similarity	NPD7328	Approved
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6607	Remote Similarity	NPD8377	Approved
0.6607	Remote Similarity	NPD8294	Approved
0.6566	Remote Similarity	NPD7991	Discontinued
0.6549	Remote Similarity	NPD8033	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.6512	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3703	Phase 2
0.6477	Remote Similarity	NPD3702	Approved
0.6476	Remote Similarity	NPD6008	Approved
0.6452	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3669	Approved
0.6421	Remote Similarity	NPD8308	Discontinued
0.6415	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2686	Approved
0.6395	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4787	Phase 1
0.6395	Remote Similarity	NPD2687	Approved
0.6395	Remote Similarity	NPD2254	Approved
0.6373	Remote Similarity	NPD7638	Approved
0.6353	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5360	Phase 3
0.6322	Remote Similarity	NPD6081	Approved
0.6316	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD7639	Approved
0.6304	Remote Similarity	NPD7525	Registered
0.6279	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8297	Approved
0.6265	Remote Similarity	NPD371	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD1779	Approved
0.6237	Remote Similarity	NPD1780	Approved
0.6218	Remote Similarity	NPD7736	Approved
0.6204	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7632	Discontinued
0.6186	Remote Similarity	NPD7507	Approved
0.6167	Remote Similarity	NPD7319	Approved
0.6154	Remote Similarity	NPD8418	Phase 2
0.6147	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8293	Discontinued
0.6118	Remote Similarity	NPD4224	Phase 2
0.6106	Remote Similarity	NPD6940	Discontinued
0.6102	Remote Similarity	NPD7492	Approved
0.6078	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6051	Approved
0.6055	Remote Similarity	NPD7320	Approved
0.605	Remote Similarity	NPD6616	Approved
0.604	Remote Similarity	NPD6399	Phase 3
0.6034	Remote Similarity	NPD6059	Approved
0.6034	Remote Similarity	NPD6054	Approved
0.6034	Remote Similarity	NPD6319	Approved
0.6023	Remote Similarity	NPD4789	Approved
0.6023	Remote Similarity	NPD4245	Approved
0.6023	Remote Similarity	NPD4244	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD1811	Approved
0.6	Remote Similarity	NPD1810	Approved
0.6	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5983	Remote Similarity	NPD7503	Approved
0.598	Remote Similarity	NPD7900	Approved
0.598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4758	Discontinued
0.5932	Remote Similarity	NPD6370	Approved
0.5929	Remote Similarity	NPD4632	Approved
0.5914	Remote Similarity	NPD5364	Discontinued
0.5913	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6881	Approved
0.5909	Remote Similarity	NPD6899	Approved
0.5909	Remote Similarity	NPD3698	Phase 2
0.5893	Remote Similarity	NPD8130	Phase 1
0.5893	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6650	Approved
0.5876	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7524	Approved
0.5847	Remote Similarity	NPD6016	Approved
0.5847	Remote Similarity	NPD6015	Approved
0.5841	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD7748	Approved
0.5818	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD5701	Approved
0.5814	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7902	Approved
0.5804	Remote Similarity	NPD7102	Approved
0.5804	Remote Similarity	NPD7290	Approved
0.5804	Remote Similarity	NPD6883	Approved
0.58	Remote Similarity	NPD5737	Approved
0.58	Remote Similarity	NPD6672	Approved
0.58	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6903	Approved
0.5798	Remote Similarity	NPD5988	Approved
0.5795	Remote Similarity	NPD229	Approved
0.5776	Remote Similarity	NPD6009	Approved
0.5773	Remote Similarity	NPD6695	Phase 3
0.5766	Remote Similarity	NPD8174	Phase 2
0.5758	Remote Similarity	NPD7521	Approved
0.5758	Remote Similarity	NPD5330	Approved
0.5758	Remote Similarity	NPD7334	Approved
0.5758	Remote Similarity	NPD7146	Approved
0.5758	Remote Similarity	NPD6409	Approved
0.5758	Remote Similarity	NPD6684	Approved
0.5752	Remote Similarity	NPD6617	Approved
0.5752	Remote Similarity	NPD6869	Approved
0.5752	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD7604	Phase 2
0.5745	Remote Similarity	NPD3671	Phase 1
0.5714	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD6921	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.57	Remote Similarity	NPD7750	Discontinued
0.5688	Remote Similarity	NPD7987	Approved
0.5688	Remote Similarity	NPD7911	Approved
0.5688	Remote Similarity	NPD7912	Approved
0.5688	Remote Similarity	NPD7986	Approved
0.5686	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6700	Approved
0.5676	Remote Similarity	NPD6412	Phase 2
0.5673	Remote Similarity	NPD6001	Approved
0.566	Remote Similarity	NPD6084	Phase 2
0.566	Remote Similarity	NPD6083	Phase 2
0.5656	Remote Similarity	NPD6336	Discontinued
0.5641	Remote Similarity	NPD7115	Discovery
0.5638	Remote Similarity	NPD8144	Approved
0.5638	Remote Similarity	NPD8143	Approved
0.5631	Remote Similarity	NPD6702	Approved
0.5631	Remote Similarity	NPD7637	Suspended
0.5631	Remote Similarity	NPD6703	Approved
0.5625	Remote Similarity	NPD6011	Approved
0.5625	Remote Similarity	NPD6686	Approved
0.562	Remote Similarity	NPD8328	Phase 3
0.5614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD4225	Approved
0.56	Remote Similarity	NPD6098	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