NPASS Compound

Structure

CID220379 OpenBabel06191716012D 36 40 0 0 1 0 0 0 0 0999 V2000 3.2909 -4.8158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2735 -1.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7808 -1.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8550 3.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4122 2.4707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6448 -0.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 -2.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8224 0.5040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6947 0.9790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.8995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8221 -1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2893 0.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4666 -0.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4679 -3.3224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2890 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6456 -2.8483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6445 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8229 1.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1430 -4.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 1.4233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6453 0.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4669 -1.4239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8229 -1.4244 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8224 -0.4751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2898 -2.8473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2892 -1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 2.3721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6451 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6450 -1.8990 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8227 -0.4746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9956 -4.8148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 1.4374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6020 2.7585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1424 -3.3390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 31 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 33 2 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 29 1 6 0 0 0 22 27 1 0 0 0 0 22 30 1 1 0 0 0 23 30 1 1 0 0 0 23 31 1 0 0 0 0 24 29 1 6 0 0 0 24 32 1 0 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 26 36 1 1 0 0 0 28 35 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 1 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.4
Volume:	551.77
LogP:	5.625
LogD:	4.985
LogS:	-4.985
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.966
Fsp3:	0.969
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.877
MDCK Permeability:	4.4253676605876535e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.336
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	91.03617095947266%
Volume Distribution (VD):	1.05
Pgp-substrate:	2.4147086143493652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.465

ADMET: Excretion

Clearance (CL):	3.894
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.564
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.933
Carcinogencity:	0.022
Eye Corrosion:	0.967
Eye Irritation:	0.175
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC220379

Natural Product ID:	NPC220379
*Common Name:**	3Beta-Acetoxy-15Alpha,22-Dihydroxyhopane
IUPAC Name:	[(3S,3aS,5S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-5-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
Synonyms:
Standard InCHIKey:	YVAGCSJSVHJSNX-CSTUNLOWSA-N
Standard InCHI:	InChI=1S/C32H54O4/c1-19(33)36-26-14-16-30(7)22(27(26,2)3)13-17-31(8)23(30)10-11-24-29(6)15-12-20(28(4,5)35)21(29)18-25(34)32(24,31)9/h20-26,34-35H,10-18H2,1-9H3/t20-,21-,22-,23+,24+,25-,26-,29-,30-,31+,32-/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)[C@@H](O)C[C@@H]1[C@]2(C)CC[C@@H]1C(O)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928584
PubChem CID:	57398931
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids

*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
NPO30117	Hypocrella	Genus	Clavicipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21995505]
NPO33604	Hypocrella sp. BCC 14524	Species	Clavicipitaceae	Eukaryota	n.a.	The fungus used in this study was isolated from a scale insect collected in Nam Nao National Park, Phetcha Bun Province, Thailand	n.a.	PMID[21995505]
NPO30414	Moelleriella	Genus	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21995505]
NPO29992	Aschersonia	Genus	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21995505]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[454970]

☑ 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 NPC220379 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	380
0.1-0.2	3507
0.2-0.3	13378
0.3-0.4	11111
0.4-0.5	5223
0.5-0.6	4101
0.6-0.7	3738
0.7-0.8	1116
0.8-0.85	98
0.85-0.9	42
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC73515
0.9459	High Similarity	NPC212453
0.9079	High Similarity	NPC471045
0.8987	High Similarity	NPC477285
0.8987	High Similarity	NPC111582
0.8974	High Similarity	NPC190940
0.8961	High Similarity	NPC476176
0.8904	High Similarity	NPC192192
0.8861	High Similarity	NPC60018
0.8861	High Similarity	NPC202688
0.8861	High Similarity	NPC154043
0.8861	High Similarity	NPC477286
0.8861	High Similarity	NPC286719
0.8846	High Similarity	NPC261616
0.88	High Similarity	NPC74639
0.8784	High Similarity	NPC127094
0.8767	High Similarity	NPC129829
0.8767	High Similarity	NPC254037
0.8718	High Similarity	NPC201276
0.8718	High Similarity	NPC80891
0.8684	High Similarity	NPC186851
0.8659	High Similarity	NPC215968
0.8659	High Similarity	NPC155531
0.8625	High Similarity	NPC289486
0.8625	High Similarity	NPC61107
0.859	High Similarity	NPC324700
0.859	High Similarity	NPC224802
0.859	High Similarity	NPC80089
0.859	High Similarity	NPC171426
0.859	High Similarity	NPC34046
0.8537	High Similarity	NPC266651
0.8533	High Similarity	NPC157422
0.8533	High Similarity	NPC470071
0.8533	High Similarity	NPC187471
0.8533	High Similarity	NPC252182
0.8533	High Similarity	NPC100586
0.8533	High Similarity	NPC109457
0.8533	High Similarity	NPC1340
0.8519	High Similarity	NPC5280
0.8514	High Similarity	NPC66407
0.8493	Intermediate Similarity	NPC48079
0.8481	Intermediate Similarity	NPC477287
0.8462	Intermediate Similarity	NPC143133
0.8462	Intermediate Similarity	NPC171658
0.8462	Intermediate Similarity	NPC298168
0.8434	Intermediate Similarity	NPC103782
0.8434	Intermediate Similarity	NPC114378
0.8434	Intermediate Similarity	NPC477283
0.8434	Intermediate Similarity	NPC168231
0.8415	Intermediate Similarity	NPC471044
0.8415	Intermediate Similarity	NPC473336
0.84	Intermediate Similarity	NPC282454
0.8395	Intermediate Similarity	NPC208912
0.8395	Intermediate Similarity	NPC2096
0.8378	Intermediate Similarity	NPC472741
0.8375	Intermediate Similarity	NPC474714
0.8356	Intermediate Similarity	NPC142712
0.8333	Intermediate Similarity	NPC4209
0.8312	Intermediate Similarity	NPC272359
0.8312	Intermediate Similarity	NPC477508
0.8293	Intermediate Similarity	NPC474284
0.8293	Intermediate Similarity	NPC475820
0.8293	Intermediate Similarity	NPC474346
0.8293	Intermediate Similarity	NPC474253
0.8293	Intermediate Similarity	NPC213737
0.8293	Intermediate Similarity	NPC473742
0.8289	Intermediate Similarity	NPC473279
0.8272	Intermediate Similarity	NPC58631
0.8243	Intermediate Similarity	NPC476928
0.8235	Intermediate Similarity	NPC201607
0.8235	Intermediate Similarity	NPC56777
0.8228	Intermediate Similarity	NPC317913
0.8228	Intermediate Similarity	NPC133596
0.8228	Intermediate Similarity	NPC11907
0.8228	Intermediate Similarity	NPC474574
0.8228	Intermediate Similarity	NPC207010
0.8228	Intermediate Similarity	NPC64081
0.8205	Intermediate Similarity	NPC212733
0.8205	Intermediate Similarity	NPC231680
0.8205	Intermediate Similarity	NPC91387
0.8205	Intermediate Similarity	NPC270306
0.8193	Intermediate Similarity	NPC299963
0.8193	Intermediate Similarity	NPC473299
0.8182	Intermediate Similarity	NPC151214
0.8182	Intermediate Similarity	NPC153719
0.8182	Intermediate Similarity	NPC191915
0.8171	Intermediate Similarity	NPC121121
0.8171	Intermediate Similarity	NPC268040
0.8171	Intermediate Similarity	NPC472504
0.8171	Intermediate Similarity	NPC477284
0.8171	Intermediate Similarity	NPC30583
0.8161	Intermediate Similarity	NPC473066
0.8158	Intermediate Similarity	NPC231945
0.8158	Intermediate Similarity	NPC232925
0.8158	Intermediate Similarity	NPC63588
0.8158	Intermediate Similarity	NPC251201
0.8148	Intermediate Similarity	NPC304194
0.8148	Intermediate Similarity	NPC206735
0.8125	Intermediate Similarity	NPC31031
0.8125	Intermediate Similarity	NPC243594
0.8118	Intermediate Similarity	NPC252714
0.809	Intermediate Similarity	NPC94582
0.809	Intermediate Similarity	NPC57964
0.8077	Intermediate Similarity	NPC280026
0.8077	Intermediate Similarity	NPC472945
0.8077	Intermediate Similarity	NPC472944
0.8077	Intermediate Similarity	NPC167702
0.8077	Intermediate Similarity	NPC304499
0.8052	Intermediate Similarity	NPC195530
0.8052	Intermediate Similarity	NPC157777
0.8052	Intermediate Similarity	NPC131506
0.8049	Intermediate Similarity	NPC48756
0.8049	Intermediate Similarity	NPC12933
0.8049	Intermediate Similarity	NPC280781
0.8049	Intermediate Similarity	NPC476071
0.8046	Intermediate Similarity	NPC10274
0.8046	Intermediate Similarity	NPC77756
0.8026	Intermediate Similarity	NPC107919
0.8026	Intermediate Similarity	NPC477820
0.8025	Intermediate Similarity	NPC320144
0.8025	Intermediate Similarity	NPC305835
0.8025	Intermediate Similarity	NPC477282
0.8025	Intermediate Similarity	NPC81074
0.8023	Intermediate Similarity	NPC4309
0.8	Intermediate Similarity	NPC238796
0.8	Intermediate Similarity	NPC252056
0.8	Intermediate Similarity	NPC23884
0.8	Intermediate Similarity	NPC472272
0.8	Intermediate Similarity	NPC237071
0.8	Intermediate Similarity	NPC476233
0.8	Intermediate Similarity	NPC203434
0.8	Intermediate Similarity	NPC156377
0.7976	Intermediate Similarity	NPC219535
0.7976	Intermediate Similarity	NPC237938
0.7976	Intermediate Similarity	NPC319909
0.7975	Intermediate Similarity	NPC174964
0.7975	Intermediate Similarity	NPC243027
0.7975	Intermediate Similarity	NPC317242
0.7975	Intermediate Similarity	NPC195155
0.7975	Intermediate Similarity	NPC196136
0.7975	Intermediate Similarity	NPC478105
0.7975	Intermediate Similarity	NPC158208
0.7975	Intermediate Similarity	NPC97534
0.7955	Intermediate Similarity	NPC219516
0.7952	Intermediate Similarity	NPC242771
0.7952	Intermediate Similarity	NPC296734
0.7952	Intermediate Similarity	NPC311642
0.7952	Intermediate Similarity	NPC100366
0.7952	Intermediate Similarity	NPC164289
0.7949	Intermediate Similarity	NPC470610
0.7949	Intermediate Similarity	NPC472341
0.7949	Intermediate Similarity	NPC473238
0.7945	Intermediate Similarity	NPC114891
0.7927	Intermediate Similarity	NPC477851
0.7927	Intermediate Similarity	NPC472943
0.7927	Intermediate Similarity	NPC475456
0.7927	Intermediate Similarity	NPC472951
0.7907	Intermediate Similarity	NPC140446
0.7907	Intermediate Similarity	NPC5943
0.7907	Intermediate Similarity	NPC43912
0.7907	Intermediate Similarity	NPC33768
0.7901	Intermediate Similarity	NPC185465
0.7901	Intermediate Similarity	NPC471769
0.7889	Intermediate Similarity	NPC279974
0.7882	Intermediate Similarity	NPC290612
0.7875	Intermediate Similarity	NPC5767
0.7875	Intermediate Similarity	NPC163597
0.7875	Intermediate Similarity	NPC475742
0.7865	Intermediate Similarity	NPC287118
0.7865	Intermediate Similarity	NPC471902
0.7865	Intermediate Similarity	NPC473690
0.7865	Intermediate Similarity	NPC256104
0.7865	Intermediate Similarity	NPC182740
0.7865	Intermediate Similarity	NPC211845
0.7865	Intermediate Similarity	NPC122083
0.7857	Intermediate Similarity	NPC470070
0.7848	Intermediate Similarity	NPC10476
0.7848	Intermediate Similarity	NPC48795
0.7848	Intermediate Similarity	NPC192501
0.7848	Intermediate Similarity	NPC228994
0.7841	Intermediate Similarity	NPC185529
0.7841	Intermediate Similarity	NPC472146
0.7821	Intermediate Similarity	NPC469940
0.7816	Intermediate Similarity	NPC160304
0.7808	Intermediate Similarity	NPC218585
0.7808	Intermediate Similarity	NPC148174
0.7808	Intermediate Similarity	NPC71460
0.7805	Intermediate Similarity	NPC73013
0.7802	Intermediate Similarity	NPC296936
0.7802	Intermediate Similarity	NPC304899
0.7802	Intermediate Similarity	NPC253115
0.7792	Intermediate Similarity	NPC299948
0.7792	Intermediate Similarity	NPC99264
0.7792	Intermediate Similarity	NPC241085
0.7792	Intermediate Similarity	NPC470830
0.7791	Intermediate Similarity	NPC171698
0.7791	Intermediate Similarity	NPC131365
0.7791	Intermediate Similarity	NPC83242
0.7791	Intermediate Similarity	NPC321340
0.7791	Intermediate Similarity	NPC12774

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 NPC220379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	3728
0.2-0.3	3481
0.3-0.4	953
0.4-0.5	262
0.5-0.6	204
0.6-0.7	110
0.7-0.8	23
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD6114	Approved
0.859	High Similarity	NPD6118	Approved
0.859	High Similarity	NPD6115	Approved
0.859	High Similarity	NPD6697	Approved
0.8333	Intermediate Similarity	NPD6117	Approved
0.8228	Intermediate Similarity	NPD6116	Phase 1
0.8077	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD8034	Phase 2
0.7753	Intermediate Similarity	NPD8035	Phase 2
0.7711	Intermediate Similarity	NPD6928	Phase 2
0.7674	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3703	Phase 2
0.7468	Intermediate Similarity	NPD4787	Phase 1
0.7342	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3702	Approved
0.7215	Intermediate Similarity	NPD5360	Phase 3
0.7215	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5777	Approved
0.716	Intermediate Similarity	NPD6081	Approved
0.7097	Intermediate Similarity	NPD8171	Discontinued
0.7093	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD4244	Approved
0.7037	Intermediate Similarity	NPD4789	Approved
0.7037	Intermediate Similarity	NPD4245	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.701	Intermediate Similarity	NPD8418	Phase 2
0.701	Intermediate Similarity	NPD7639	Approved
0.6962	Remote Similarity	NPD4224	Phase 2
0.6914	Remote Similarity	NPD3698	Phase 2
0.6869	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD7748	Approved
0.6835	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7991	Discontinued
0.6747	Remote Similarity	NPD4758	Discontinued
0.6733	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5364	Discontinued
0.6667	Remote Similarity	NPD3671	Phase 1
0.6633	Remote Similarity	NPD7902	Approved
0.6632	Remote Similarity	NPD7515	Phase 2
0.6591	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD6399	Phase 3
0.6542	Remote Similarity	NPD8133	Approved
0.6526	Remote Similarity	NPD6700	Approved
0.6526	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6675	Approved
0.6505	Remote Similarity	NPD6402	Approved
0.6505	Remote Similarity	NPD7128	Approved
0.6505	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD8294	Approved
0.6486	Remote Similarity	NPD8377	Approved
0.6458	Remote Similarity	NPD6703	Approved
0.6458	Remote Similarity	NPD6702	Approved
0.6455	Remote Similarity	NPD7327	Approved
0.6455	Remote Similarity	NPD7328	Approved
0.6452	Remote Similarity	NPD8308	Discontinued
0.6429	Remote Similarity	NPD8378	Approved
0.6429	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD8296	Approved
0.6429	Remote Similarity	NPD8380	Approved
0.6429	Remote Similarity	NPD8379	Approved
0.6429	Remote Similarity	NPD8335	Approved
0.6396	Remote Similarity	NPD7516	Approved
0.6381	Remote Similarity	NPD7320	Approved
0.6381	Remote Similarity	NPD6899	Approved
0.6381	Remote Similarity	NPD6881	Approved
0.6355	Remote Similarity	NPD8130	Phase 1
0.6327	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7900	Approved
0.6322	Remote Similarity	NPD6942	Approved
0.6322	Remote Similarity	NPD7339	Approved
0.6321	Remote Similarity	NPD6373	Approved
0.6321	Remote Similarity	NPD6372	Approved
0.6304	Remote Similarity	NPD6695	Phase 3
0.6304	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4788	Approved
0.6304	Remote Similarity	NPD3669	Approved
0.63	Remote Similarity	NPD6083	Phase 2
0.63	Remote Similarity	NPD6084	Phase 2
0.6296	Remote Similarity	NPD8297	Approved
0.6296	Remote Similarity	NPD371	Approved
0.6286	Remote Similarity	NPD5697	Approved
0.6286	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5701	Approved
0.6273	Remote Similarity	NPD6940	Discontinued
0.6262	Remote Similarity	NPD7290	Approved
0.6262	Remote Similarity	NPD7102	Approved
0.6262	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD5328	Approved
0.6237	Remote Similarity	NPD4786	Approved
0.6237	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6011	Approved
0.6211	Remote Similarity	NPD7750	Discontinued
0.6207	Remote Similarity	NPD1811	Approved
0.6207	Remote Similarity	NPD1810	Approved
0.6204	Remote Similarity	NPD6649	Approved
0.6204	Remote Similarity	NPD6869	Approved
0.6204	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6847	Approved
0.6204	Remote Similarity	NPD6617	Approved
0.6204	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD6920	Discontinued
0.619	Remote Similarity	NPD6705	Phase 1
0.6168	Remote Similarity	NPD6014	Approved
0.6168	Remote Similarity	NPD6012	Approved
0.6168	Remote Similarity	NPD6013	Approved
0.6168	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4748	Discontinued
0.6147	Remote Similarity	NPD6882	Approved
0.6146	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6079	Approved
0.6122	Remote Similarity	NPD7637	Suspended
0.6117	Remote Similarity	NPD1700	Approved
0.6105	Remote Similarity	NPD3618	Phase 1
0.6102	Remote Similarity	NPD7736	Approved
0.6091	Remote Similarity	NPD8298	Phase 2
0.6091	Remote Similarity	NPD4632	Approved
0.6075	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7115	Discovery
0.6068	Remote Similarity	NPD7507	Approved
0.6067	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4202	Approved
0.6047	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7524	Approved
0.6042	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6008	Approved
0.6023	Remote Similarity	NPD6924	Approved
0.6023	Remote Similarity	NPD6926	Approved
0.6022	Remote Similarity	NPD3667	Approved
0.6019	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7911	Approved
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD7912	Approved
0.6	Remote Similarity	NPD7986	Approved
0.6	Remote Similarity	NPD3198	Approved
0.6	Remote Similarity	NPD7987	Approved
0.5982	Remote Similarity	NPD7755	Approved
0.5982	Remote Similarity	NPD7754	Approved
0.598	Remote Similarity	NPD4755	Approved
0.598	Remote Similarity	NPD7919	Phase 3
0.598	Remote Similarity	NPD7920	Phase 3
0.5979	Remote Similarity	NPD6672	Approved
0.5979	Remote Similarity	NPD5737	Approved
0.5978	Remote Similarity	NPD6931	Approved
0.5978	Remote Similarity	NPD6930	Phase 2
0.5941	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5695	Phase 3
0.5938	Remote Similarity	NPD7146	Approved
0.5938	Remote Similarity	NPD7521	Approved
0.5938	Remote Similarity	NPD6409	Approved
0.5938	Remote Similarity	NPD5330	Approved
0.5938	Remote Similarity	NPD6684	Approved
0.5938	Remote Similarity	NPD7334	Approved
0.5934	Remote Similarity	NPD4802	Phase 2
0.5934	Remote Similarity	NPD4238	Approved
0.5929	Remote Similarity	NPD6009	Approved
0.5922	Remote Similarity	NPD8088	Phase 1
0.5922	Remote Similarity	NPD5696	Approved
0.5917	Remote Similarity	NPD7319	Approved
0.5913	Remote Similarity	NPD6319	Approved
0.5897	Remote Similarity	NPD7604	Phase 2
0.589	Remote Similarity	NPD385	Approved
0.589	Remote Similarity	NPD384	Approved
0.5889	Remote Similarity	NPD6933	Approved
0.5888	Remote Similarity	NPD8040	Discontinued
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD5221	Approved
0.5882	Remote Similarity	NPD5222	Approved
0.5882	Remote Similarity	NPD8293	Discontinued
0.5877	Remote Similarity	NPD6335	Approved
0.587	Remote Similarity	NPD6929	Approved
0.5865	Remote Similarity	NPD5285	Approved
0.5865	Remote Similarity	NPD4700	Approved
0.5865	Remote Similarity	NPD4696	Approved
0.5865	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD2686	Approved
0.5862	Remote Similarity	NPD2687	Approved
0.5862	Remote Similarity	NPD2254	Approved
0.5862	Remote Similarity	NPD5983	Phase 2
0.5847	Remote Similarity	NPD7492	Approved
0.5841	Remote Similarity	NPD6274	Approved
0.5841	Remote Similarity	NPD6868	Approved
0.5833	Remote Similarity	NPD7990	Approved
0.5833	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD7989	Approved
0.5826	Remote Similarity	NPD7101	Approved
0.5826	Remote Similarity	NPD7100	Approved
0.5825	Remote Similarity	NPD5173	Approved
0.5824	Remote Similarity	NPD8143	Approved
0.5824	Remote Similarity	NPD8144	Approved
0.5824	Remote Similarity	NPD6932	Approved
0.5818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6903	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