NPASS Compound

Structure

CID129829 OpenBabel06191715492D 33 37 0 0 1 0 0 0 0 0999 V2000 4.2684 -1.8953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7764 -1.0442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8516 3.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4082 2.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6429 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7974 -2.3857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8214 0.5028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.8973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8212 -1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2854 0.9471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4637 -0.4736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4650 -3.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2851 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6436 -2.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6426 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 1.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4651 1.4217 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6434 0.9476 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4640 -1.4222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8220 -1.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8214 -0.4745 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2859 -2.8440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2854 -1.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4657 2.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6431 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6431 -1.8968 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8217 -0.4741 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 4.1375 -3.3351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6002 2.7553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 27 1 6 0 0 0 20 25 1 0 0 0 0 20 28 1 1 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 27 1 6 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 30 1 6 0 0 0 24 32 1 0 0 0 0 26 33 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	511.024
LogP:	5.085
LogD:	4.906
LogS:	-4.556
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	4.948
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89
MDCK Permeability:	3.250945155741647e-05
Pgp-inhibitor:	0.923
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	93.1119384765625%
Volume Distribution (VD):	0.985
Pgp-substrate:	2.943617582321167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.329
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	5.734
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.232
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.931
Carcinogencity:	0.023
Eye Corrosion:	0.954
Eye Irritation:	0.211
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC129829

Natural Product ID:	NPC129829
*Common Name:**	3Beta,15Alpha,22-Trihydroxyhopane
IUPAC Name:	(3S,3aS,5S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-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]chrysene-5,9-diol
Synonyms:	3Beta,15Alpha,22-Trihydroxyhopane
Standard InCHIKey:	DKCBVIPOQXEXSD-NPOVCAEKSA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-25(2)20-12-16-29(7)21(28(20,6)15-13-23(25)31)9-10-22-27(5)14-11-18(26(3,4)33)19(27)17-24(32)30(22,29)8/h18-24,31-33H,9-17H2,1-8H3/t18-,19-,20-,21+,22+,23-,24-,27-,28-,29+,30-/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@H]5C[C@@H]([C@@]34C)O)C(C)(C)O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928583
PubChem CID:	57397239
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]

☑ 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	>	50.0	ug.mL-1	PMID[489115]

☑ 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 NPC129829 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	391
0.1-0.2	4783
0.2-0.3	16913
0.3-0.4	8780
0.4-0.5	4551
0.5-0.6	4124
0.6-0.7	2289
0.7-0.8	675
0.8-0.85	111
0.85-0.9	59
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254037
0.9846	High Similarity	NPC192192
0.9697	High Similarity	NPC127094
0.9688	High Similarity	NPC48079
0.9538	High Similarity	NPC472741
0.9531	High Similarity	NPC142712
0.9394	High Similarity	NPC66407
0.9254	High Similarity	NPC231945
0.9118	High Similarity	NPC252182
0.9118	High Similarity	NPC187471
0.9118	High Similarity	NPC470071
0.9118	High Similarity	NPC1340
0.9104	High Similarity	NPC477820
0.9062	High Similarity	NPC114891
0.8986	High Similarity	NPC153719
0.8971	High Similarity	NPC251201
0.8971	High Similarity	NPC63588
0.8971	High Similarity	NPC282454
0.8971	High Similarity	NPC232925
0.8906	High Similarity	NPC71460
0.8906	High Similarity	NPC148174
0.8906	High Similarity	NPC218585
0.8857	High Similarity	NPC192501
0.8857	High Similarity	NPC10476
0.8857	High Similarity	NPC228994
0.8857	High Similarity	NPC304499
0.8857	High Similarity	NPC477508
0.8841	High Similarity	NPC157422
0.8841	High Similarity	NPC100586
0.8841	High Similarity	NPC109457
0.8841	High Similarity	NPC473279
0.8824	High Similarity	NPC241085
0.8824	High Similarity	NPC470830
0.8824	High Similarity	NPC107919
0.8824	High Similarity	NPC299948
0.8806	High Similarity	NPC473230
0.8806	High Similarity	NPC475884
0.8788	High Similarity	NPC474380
0.8788	High Similarity	NPC41577
0.8788	High Similarity	NPC260116
0.8788	High Similarity	NPC473276
0.8788	High Similarity	NPC80463
0.8767	High Similarity	NPC220379
0.875	High Similarity	NPC202540
0.8732	High Similarity	NPC270306
0.8732	High Similarity	NPC243027
0.8732	High Similarity	NPC231680
0.8732	High Similarity	NPC317242
0.8732	High Similarity	NPC158208
0.8732	High Similarity	NPC196136
0.8732	High Similarity	NPC91387
0.8714	High Similarity	NPC470610
0.8676	High Similarity	NPC469987
0.8676	High Similarity	NPC474756
0.8657	High Similarity	NPC44122
0.8636	High Similarity	NPC159654
0.8636	High Similarity	NPC167995
0.8636	High Similarity	NPC118937
0.8636	High Similarity	NPC281540
0.8636	High Similarity	NPC69149
0.8611	High Similarity	NPC163597
0.8592	High Similarity	NPC48795
0.8571	High Similarity	NPC195530
0.8533	High Similarity	NPC73515
0.8529	High Similarity	NPC63190
0.8514	High Similarity	NPC472742
0.8514	High Similarity	NPC80297
0.8514	High Similarity	NPC116119
0.8514	High Similarity	NPC475727
0.8493	Intermediate Similarity	NPC302578
0.8493	Intermediate Similarity	NPC23884
0.8493	Intermediate Similarity	NPC477227
0.8493	Intermediate Similarity	NPC64081
0.8493	Intermediate Similarity	NPC474574
0.8493	Intermediate Similarity	NPC128951
0.8493	Intermediate Similarity	NPC133596
0.8493	Intermediate Similarity	NPC11907
0.8493	Intermediate Similarity	NPC185915
0.8493	Intermediate Similarity	NPC476233
0.8493	Intermediate Similarity	NPC192046
0.8493	Intermediate Similarity	NPC105208
0.8485	Intermediate Similarity	NPC209686
0.8485	Intermediate Similarity	NPC236099
0.8485	Intermediate Similarity	NPC292419
0.8485	Intermediate Similarity	NPC249078
0.8485	Intermediate Similarity	NPC290791
0.8472	Intermediate Similarity	NPC174964
0.8472	Intermediate Similarity	NPC240235
0.8472	Intermediate Similarity	NPC195155
0.8472	Intermediate Similarity	NPC178383
0.8472	Intermediate Similarity	NPC212879
0.8472	Intermediate Similarity	NPC231256
0.8472	Intermediate Similarity	NPC97534
0.8472	Intermediate Similarity	NPC104387
0.8451	Intermediate Similarity	NPC472341
0.8451	Intermediate Similarity	NPC473238
0.8438	Intermediate Similarity	NPC476735
0.8438	Intermediate Similarity	NPC162685
0.8421	Intermediate Similarity	NPC268040
0.8406	Intermediate Similarity	NPC475893
0.84	Intermediate Similarity	NPC475679
0.8378	Intermediate Similarity	NPC42853
0.8378	Intermediate Similarity	NPC471769
0.8378	Intermediate Similarity	NPC31828
0.8378	Intermediate Similarity	NPC67657
0.8378	Intermediate Similarity	NPC18857
0.8378	Intermediate Similarity	NPC147993
0.8356	Intermediate Similarity	NPC475742
0.8356	Intermediate Similarity	NPC473916
0.8356	Intermediate Similarity	NPC78067
0.8356	Intermediate Similarity	NPC477602
0.8356	Intermediate Similarity	NPC86305
0.8356	Intermediate Similarity	NPC477601
0.8356	Intermediate Similarity	NPC5767
0.8356	Intermediate Similarity	NPC278091
0.8356	Intermediate Similarity	NPC93662
0.8356	Intermediate Similarity	NPC14112
0.8333	Intermediate Similarity	NPC192638
0.8333	Intermediate Similarity	NPC308440
0.8333	Intermediate Similarity	NPC25511
0.8333	Intermediate Similarity	NPC62657
0.8333	Intermediate Similarity	NPC472503
0.831	Intermediate Similarity	NPC478103
0.831	Intermediate Similarity	NPC131506
0.831	Intermediate Similarity	NPC157777
0.8286	Intermediate Similarity	NPC99264
0.8286	Intermediate Similarity	NPC470833
0.8281	Intermediate Similarity	NPC135438
0.8267	Intermediate Similarity	NPC49627
0.8267	Intermediate Similarity	NPC49599
0.8267	Intermediate Similarity	NPC287452
0.8267	Intermediate Similarity	NPC81074
0.8267	Intermediate Similarity	NPC477282
0.8261	Intermediate Similarity	NPC204233
0.8243	Intermediate Similarity	NPC143133
0.8243	Intermediate Similarity	NPC119355
0.8243	Intermediate Similarity	NPC212241
0.8243	Intermediate Similarity	NPC248830
0.8243	Intermediate Similarity	NPC212453
0.8243	Intermediate Similarity	NPC221420
0.8243	Intermediate Similarity	NPC298168
0.8235	Intermediate Similarity	NPC475943
0.8235	Intermediate Similarity	NPC190827
0.8235	Intermediate Similarity	NPC243469
0.8219	Intermediate Similarity	NPC3403
0.8219	Intermediate Similarity	NPC103822
0.8194	Intermediate Similarity	NPC253805
0.8194	Intermediate Similarity	NPC232112
0.8158	Intermediate Similarity	NPC16449
0.8133	Intermediate Similarity	NPC80089
0.8133	Intermediate Similarity	NPC224802
0.8133	Intermediate Similarity	NPC477819
0.8133	Intermediate Similarity	NPC171426
0.8133	Intermediate Similarity	NPC477817
0.8133	Intermediate Similarity	NPC324700
0.8133	Intermediate Similarity	NPC102708
0.8133	Intermediate Similarity	NPC471045
0.8133	Intermediate Similarity	NPC34046
0.8108	Intermediate Similarity	NPC91573
0.8108	Intermediate Similarity	NPC470145
0.8082	Intermediate Similarity	NPC478130
0.8082	Intermediate Similarity	NPC475458
0.8077	Intermediate Similarity	NPC470929
0.806	Intermediate Similarity	NPC185547
0.806	Intermediate Similarity	NPC95804
0.8056	Intermediate Similarity	NPC111234
0.8056	Intermediate Similarity	NPC320549
0.8056	Intermediate Similarity	NPC151018
0.8056	Intermediate Similarity	NPC156277
0.8056	Intermediate Similarity	NPC127283
0.8056	Intermediate Similarity	NPC58057
0.8056	Intermediate Similarity	NPC8004
0.803	Intermediate Similarity	NPC95958
0.8026	Intermediate Similarity	NPC476176
0.8026	Intermediate Similarity	NPC80891
0.8026	Intermediate Similarity	NPC201276
0.8	Intermediate Similarity	NPC236588
0.8	Intermediate Similarity	NPC475031
0.7973	Intermediate Similarity	NPC185536
0.7973	Intermediate Similarity	NPC159789
0.7973	Intermediate Similarity	NPC230704
0.7973	Intermediate Similarity	NPC273366
0.7973	Intermediate Similarity	NPC186851
0.7973	Intermediate Similarity	NPC70982
0.7973	Intermediate Similarity	NPC212733
0.7971	Intermediate Similarity	NPC472946
0.7949	Intermediate Similarity	NPC202688
0.7949	Intermediate Similarity	NPC475388
0.7949	Intermediate Similarity	NPC60018
0.7949	Intermediate Similarity	NPC154043
0.7949	Intermediate Similarity	NPC296734
0.7922	Intermediate Similarity	NPC7479
0.7922	Intermediate Similarity	NPC257296
0.7922	Intermediate Similarity	NPC78545
0.7922	Intermediate Similarity	NPC248944
0.7922	Intermediate Similarity	NPC71535
0.7917	Intermediate Similarity	NPC45296
0.7895	Intermediate Similarity	NPC472500
0.7895	Intermediate Similarity	NPC472342
0.7895	Intermediate Similarity	NPC477577

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 NPC129829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	4516
0.2-0.3	3025
0.3-0.4	720
0.4-0.5	180
0.5-0.6	207
0.6-0.7	66
0.7-0.8	20
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD4267	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD4787	Phase 1
0.8133	Intermediate Similarity	NPD6118	Approved
0.8133	Intermediate Similarity	NPD6114	Approved
0.8133	Intermediate Similarity	NPD6697	Approved
0.8133	Intermediate Similarity	NPD6115	Approved
0.8056	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3703	Phase 2
0.7922	Intermediate Similarity	NPD6928	Phase 2
0.7867	Intermediate Similarity	NPD6117	Approved
0.7838	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6116	Phase 1
0.7692	Intermediate Similarity	NPD7525	Registered
0.7639	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5360	Phase 3
0.7439	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4244	Approved
0.7432	Intermediate Similarity	NPD4245	Approved
0.7432	Intermediate Similarity	NPD4789	Approved
0.7297	Intermediate Similarity	NPD3698	Phase 2
0.7222	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7645	Phase 2
0.7105	Intermediate Similarity	NPD4758	Discontinued
0.7051	Intermediate Similarity	NPD7339	Approved
0.7051	Intermediate Similarity	NPD6942	Approved
0.7011	Intermediate Similarity	NPD6701	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6700	Approved
0.7	Intermediate Similarity	NPD3671	Phase 1
0.6933	Remote Similarity	NPD6705	Phase 1
0.6932	Remote Similarity	NPD6703	Approved
0.6932	Remote Similarity	NPD6702	Approved
0.6854	Remote Similarity	NPD8171	Discontinued
0.6829	Remote Similarity	NPD4748	Discontinued
0.679	Remote Similarity	NPD5364	Discontinued
0.675	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8034	Phase 2
0.6742	Remote Similarity	NPD8035	Phase 2
0.6719	Remote Similarity	NPD385	Approved
0.6719	Remote Similarity	NPD384	Approved
0.6709	Remote Similarity	NPD6924	Approved
0.6709	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6627	Remote Similarity	NPD6931	Approved
0.6627	Remote Similarity	NPD6930	Phase 2
0.6625	Remote Similarity	NPD3702	Approved
0.6622	Remote Similarity	NPD371	Approved
0.6588	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD388	Approved
0.6562	Remote Similarity	NPD386	Approved
0.6552	Remote Similarity	NPD8308	Discontinued
0.6543	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD7991	Discontinued
0.6517	Remote Similarity	NPD5328	Approved
0.6512	Remote Similarity	NPD4786	Approved
0.6506	Remote Similarity	NPD6929	Approved
0.6463	Remote Similarity	NPD6932	Approved
0.6456	Remote Similarity	NPD4243	Approved
0.6456	Remote Similarity	NPD5777	Approved
0.6421	Remote Similarity	NPD8418	Phase 2
0.6395	Remote Similarity	NPD6695	Phase 3
0.6374	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6322	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7638	Approved
0.631	Remote Similarity	NPD6683	Phase 2
0.6304	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD4784	Approved
0.6296	Remote Similarity	NPD4785	Approved
0.6279	Remote Similarity	NPD3667	Approved
0.6265	Remote Similarity	NPD5776	Phase 2
0.6265	Remote Similarity	NPD6925	Approved
0.625	Remote Similarity	NPD7152	Approved
0.625	Remote Similarity	NPD7151	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD6893	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6235	Remote Similarity	NPD7509	Discontinued
0.6235	Remote Similarity	NPD7514	Phase 3
0.6211	Remote Similarity	NPD7920	Phase 3
0.6211	Remote Similarity	NPD7919	Phase 3
0.6203	Remote Similarity	NPD6922	Approved
0.6203	Remote Similarity	NPD6923	Approved
0.6196	Remote Similarity	NPD7515	Phase 2
0.619	Remote Similarity	NPD7145	Approved
0.6162	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD8088	Phase 1
0.6125	Remote Similarity	NPD7144	Approved
0.6125	Remote Similarity	NPD7143	Approved
0.6122	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD7524	Approved
0.6111	Remote Similarity	NPD7750	Discontinued
0.6098	Remote Similarity	NPD1811	Approved
0.6098	Remote Similarity	NPD1810	Approved
0.6047	Remote Similarity	NPD7332	Phase 2
0.6042	Remote Similarity	NPD4755	Approved
0.6024	Remote Similarity	NPD5275	Approved
0.6024	Remote Similarity	NPD4190	Phase 3
0.5977	Remote Similarity	NPD6898	Phase 1
0.5977	Remote Similarity	NPD6902	Approved
0.5955	Remote Similarity	NPD3666	Approved
0.5955	Remote Similarity	NPD3133	Approved
0.5955	Remote Similarity	NPD3665	Phase 1
0.5941	Remote Similarity	NPD6920	Discontinued
0.5938	Remote Similarity	NPD4697	Phase 3
0.5938	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5222	Approved
0.5938	Remote Similarity	NPD5221	Approved
0.593	Remote Similarity	NPD4195	Approved
0.5918	Remote Similarity	NPD4696	Approved
0.5918	Remote Similarity	NPD5286	Approved
0.5918	Remote Similarity	NPD5285	Approved
0.5918	Remote Similarity	NPD4700	Approved
0.5895	Remote Similarity	NPD7748	Approved
0.5876	Remote Similarity	NPD5173	Approved
0.5859	Remote Similarity	NPD5223	Approved
0.5851	Remote Similarity	NPD7087	Discontinued
0.5814	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4753	Phase 2
0.58	Remote Similarity	NPD5224	Approved
0.58	Remote Similarity	NPD5211	Phase 2
0.58	Remote Similarity	NPD5226	Approved
0.58	Remote Similarity	NPD4633	Approved
0.58	Remote Similarity	NPD5225	Approved
0.5789	Remote Similarity	NPD6399	Phase 3
0.5784	Remote Similarity	NPD6402	Approved
0.5784	Remote Similarity	NPD6675	Approved
0.5784	Remote Similarity	NPD7128	Approved
0.5784	Remote Similarity	NPD5739	Approved
0.578	Remote Similarity	NPD7327	Approved
0.578	Remote Similarity	NPD7328	Approved
0.5743	Remote Similarity	NPD5174	Approved
0.5743	Remote Similarity	NPD5175	Approved
0.5743	Remote Similarity	NPD4754	Approved
0.5732	Remote Similarity	NPD2687	Approved
0.5732	Remote Similarity	NPD2254	Approved
0.5732	Remote Similarity	NPD2686	Approved
0.573	Remote Similarity	NPD4221	Approved
0.573	Remote Similarity	NPD4223	Phase 3
0.5727	Remote Similarity	NPD7516	Approved
0.5714	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD4634	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5701	Remote Similarity	NPD8133	Approved
0.57	Remote Similarity	NPD4159	Approved
0.5686	Remote Similarity	NPD5141	Approved
0.5676	Remote Similarity	NPD8377	Approved
0.5676	Remote Similarity	NPD8294	Approved
0.5673	Remote Similarity	NPD6415	Discontinued
0.5673	Remote Similarity	NPD6881	Approved
0.5673	Remote Similarity	NPD7320	Approved
0.5673	Remote Similarity	NPD6899	Approved
0.5658	Remote Similarity	NPD3198	Approved
0.5657	Remote Similarity	NPD5290	Discontinued
0.5652	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5279	Phase 3
0.5632	Remote Similarity	NPD3617	Approved
0.5631	Remote Similarity	NPD4768	Approved
0.5631	Remote Similarity	NPD4767	Approved
0.5625	Remote Similarity	NPD8380	Approved
0.5625	Remote Similarity	NPD8296	Approved
0.5625	Remote Similarity	NPD8379	Approved
0.5625	Remote Similarity	NPD8335	Approved
0.5625	Remote Similarity	NPD8033	Approved
0.5625	Remote Similarity	NPD8378	Approved
0.5619	Remote Similarity	NPD6373	Approved
0.5619	Remote Similarity	NPD6372	Approved
0.5618	Remote Similarity	NPD4692	Approved
0.5618	Remote Similarity	NPD4139	Approved
0.5604	Remote Similarity	NPD4197	Approved
0.5604	Remote Similarity	NPD3668	Phase 3

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