NPASS Compound

Structure

NPC142712 OpenBabel07101718182D 31 35 0 0 1 0 0 0 0 0999 V2000 -4.7020 -0.9411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0120 -0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1305 2.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0220 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4505 1.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7510 -0.7390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4505 0.1857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5259 -2.4306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5259 0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5259 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1004 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 18 1 1 6 0 0 0 18 30 1 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 6 0 0 0 21 25 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 6 0 0 0 24 26 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.38
Volume:	484.938
LogP:	6.206
LogD:	5.309
LogS:	-5.723
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.772
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
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:	-5.12
MDCK Permeability:	5.740071719628759e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.19
30% Bioavailability (F30%):	0.839

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	95.29955291748047%
Volume Distribution (VD):	1.279
Pgp-substrate:	1.620269775390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	3.245
Half-life (T1/2):	0.178

ADMET: Toxicity

hERG Blockers:	0.251
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.532
Skin Sensitization:	0.64
Carcinogencity:	0.002
Eye Corrosion:	0.97
Eye Irritation:	0.882
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC142712

Natural Product ID:	NPC142712
*Common Name:**	(20R)-30-Norlupane-3Alpha,20-Diol
IUPAC Name:	(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bS)-1-[(1R)-1-hydroxyethyl]-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms:
Standard InCHIKey:	QZOQRCLOUAWPGS-QFFCLUIXSA-N
Standard InCHI:	InChI=1S/C29H50O2/c1-18(30)19-10-13-26(4)16-17-28(6)20(24(19)26)8-9-22-27(5)14-12-23(31)25(2,3)21(27)11-15-29(22,28)7/h18-24,30-31H,8-17H2,1-7H3/t18-,19+,20-,21+,22-,23-,24-,26-,27+,28-,29-/m1/s1
SMILES:	C[C@H]([C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109387
PubChem CID:	76310266
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives

*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
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[567252]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[567252]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[567252]
NPT27	Others	Unspecified		Activity	=	94.2	%	PMID[567252]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3480.0	nM	PMID[567252]

☑ 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 NPC142712 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	375
0.1-0.2	4802
0.2-0.3	18084
0.3-0.4	8194
0.4-0.5	4279
0.5-0.6	4066
0.6-0.7	2133
0.7-0.8	581
0.8-0.85	93
0.85-0.9	61
0.9-0.95	23
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC48079
0.9683	High Similarity	NPC472741
0.9531	High Similarity	NPC129829
0.9531	High Similarity	NPC254037
0.9508	High Similarity	NPC114891
0.9385	High Similarity	NPC192192
0.9385	High Similarity	NPC231945
0.9344	High Similarity	NPC71460
0.9344	High Similarity	NPC218585
0.9344	High Similarity	NPC148174
0.9242	High Similarity	NPC127094
0.9219	High Similarity	NPC473230
0.9219	High Similarity	NPC475884
0.9206	High Similarity	NPC41577
0.9206	High Similarity	NPC474380
0.9206	High Similarity	NPC473276
0.9091	High Similarity	NPC282454
0.9062	High Similarity	NPC44122
0.9048	High Similarity	NPC281540
0.9048	High Similarity	NPC159654
0.9048	High Similarity	NPC167995
0.9048	High Similarity	NPC69149
0.9048	High Similarity	NPC118937
0.8971	High Similarity	NPC477508
0.8955	High Similarity	NPC100586
0.8955	High Similarity	NPC109457
0.8955	High Similarity	NPC157422
0.8955	High Similarity	NPC473279
0.8939	High Similarity	NPC66407
0.8939	High Similarity	NPC470830
0.8939	High Similarity	NPC241085
0.8939	High Similarity	NPC107919
0.8939	High Similarity	NPC299948
0.8939	High Similarity	NPC477820
0.8906	High Similarity	NPC260116
0.8906	High Similarity	NPC80463
0.8889	High Similarity	NPC290791
0.8889	High Similarity	NPC292419
0.8852	High Similarity	NPC476735
0.8841	High Similarity	NPC195155
0.8841	High Similarity	NPC240235
0.8841	High Similarity	NPC178383
0.8841	High Similarity	NPC231256
0.8841	High Similarity	NPC212879
0.8841	High Similarity	NPC104387
0.8841	High Similarity	NPC174964
0.8841	High Similarity	NPC97534
0.8806	High Similarity	NPC251201
0.8806	High Similarity	NPC232925
0.8806	High Similarity	NPC63588
0.8714	High Similarity	NPC78067
0.8714	High Similarity	NPC475742
0.8714	High Similarity	NPC5767
0.8714	High Similarity	NPC14112
0.8714	High Similarity	NPC278091
0.8714	High Similarity	NPC86305
0.8714	High Similarity	NPC93662
0.8696	High Similarity	NPC25511
0.8696	High Similarity	NPC192638
0.8696	High Similarity	NPC62657
0.8676	High Similarity	NPC195530
0.8676	High Similarity	NPC252182
0.8676	High Similarity	NPC470071
0.8676	High Similarity	NPC187471
0.8676	High Similarity	NPC1340
0.8676	High Similarity	NPC478103
0.8657	High Similarity	NPC99264
0.8636	High Similarity	NPC63190
0.8636	High Similarity	NPC204233
0.8592	High Similarity	NPC143133
0.8592	High Similarity	NPC202540
0.8592	High Similarity	NPC212241
0.8592	High Similarity	NPC221420
0.8592	High Similarity	NPC298168
0.8592	High Similarity	NPC248830
0.8592	High Similarity	NPC119355
0.8592	High Similarity	NPC23884
0.8551	High Similarity	NPC473238
0.8551	High Similarity	NPC232112
0.8551	High Similarity	NPC470610
0.8551	High Similarity	NPC472341
0.8551	High Similarity	NPC153719
0.8548	High Similarity	NPC162685
0.8507	High Similarity	NPC475893
0.8507	High Similarity	NPC469987
0.8472	Intermediate Similarity	NPC102708
0.8472	Intermediate Similarity	NPC42853
0.8429	Intermediate Similarity	NPC228994
0.8429	Intermediate Similarity	NPC478130
0.8429	Intermediate Similarity	NPC48795
0.8429	Intermediate Similarity	NPC192501
0.8429	Intermediate Similarity	NPC10476
0.8429	Intermediate Similarity	NPC304499
0.8406	Intermediate Similarity	NPC151018
0.8406	Intermediate Similarity	NPC157777
0.8406	Intermediate Similarity	NPC320549
0.8406	Intermediate Similarity	NPC111234
0.8406	Intermediate Similarity	NPC58057
0.8406	Intermediate Similarity	NPC131506
0.8406	Intermediate Similarity	NPC156277
0.8387	Intermediate Similarity	NPC135438
0.8356	Intermediate Similarity	NPC475727
0.8356	Intermediate Similarity	NPC472742
0.8356	Intermediate Similarity	NPC49599
0.8356	Intermediate Similarity	NPC220379
0.8356	Intermediate Similarity	NPC116119
0.8356	Intermediate Similarity	NPC80297
0.8356	Intermediate Similarity	NPC49627
0.8333	Intermediate Similarity	NPC243469
0.8333	Intermediate Similarity	NPC190827
0.8333	Intermediate Similarity	NPC475943
0.831	Intermediate Similarity	NPC158208
0.831	Intermediate Similarity	NPC196136
0.831	Intermediate Similarity	NPC70982
0.831	Intermediate Similarity	NPC91387
0.831	Intermediate Similarity	NPC243027
0.831	Intermediate Similarity	NPC231680
0.831	Intermediate Similarity	NPC185536
0.831	Intermediate Similarity	NPC212733
0.831	Intermediate Similarity	NPC3403
0.831	Intermediate Similarity	NPC273366
0.831	Intermediate Similarity	NPC230704
0.831	Intermediate Similarity	NPC270306
0.831	Intermediate Similarity	NPC317242
0.8308	Intermediate Similarity	NPC236099
0.8308	Intermediate Similarity	NPC209686
0.8308	Intermediate Similarity	NPC249078
0.8286	Intermediate Similarity	NPC253805
0.8261	Intermediate Similarity	NPC45296
0.8243	Intermediate Similarity	NPC475679
0.8235	Intermediate Similarity	NPC474756
0.8194	Intermediate Similarity	NPC472486
0.8194	Intermediate Similarity	NPC91573
0.8194	Intermediate Similarity	NPC163597
0.8194	Intermediate Similarity	NPC477602
0.8194	Intermediate Similarity	NPC470145
0.8194	Intermediate Similarity	NPC477601
0.8194	Intermediate Similarity	NPC4209
0.8194	Intermediate Similarity	NPC473916
0.8194	Intermediate Similarity	NPC472487
0.8169	Intermediate Similarity	NPC167702
0.8169	Intermediate Similarity	NPC254509
0.8169	Intermediate Similarity	NPC49168
0.8169	Intermediate Similarity	NPC280026
0.8169	Intermediate Similarity	NPC254340
0.8169	Intermediate Similarity	NPC145552
0.8169	Intermediate Similarity	NPC5046
0.8169	Intermediate Similarity	NPC472503
0.8169	Intermediate Similarity	NPC196358
0.8169	Intermediate Similarity	NPC308440
0.8154	Intermediate Similarity	NPC185547
0.8154	Intermediate Similarity	NPC95804
0.8143	Intermediate Similarity	NPC127283
0.8143	Intermediate Similarity	NPC89310
0.8143	Intermediate Similarity	NPC8004
0.8133	Intermediate Similarity	NPC73515
0.8125	Intermediate Similarity	NPC95958
0.8116	Intermediate Similarity	NPC213178
0.8116	Intermediate Similarity	NPC6120
0.8116	Intermediate Similarity	NPC131892
0.8116	Intermediate Similarity	NPC327728
0.8095	Intermediate Similarity	NPC236588
0.8082	Intermediate Similarity	NPC257191
0.8082	Intermediate Similarity	NPC185915
0.8082	Intermediate Similarity	NPC11907
0.8082	Intermediate Similarity	NPC476233
0.8082	Intermediate Similarity	NPC207010
0.8082	Intermediate Similarity	NPC477227
0.8082	Intermediate Similarity	NPC105208
0.8082	Intermediate Similarity	NPC302578
0.8082	Intermediate Similarity	NPC64081
0.8082	Intermediate Similarity	NPC475031
0.8082	Intermediate Similarity	NPC331618
0.8082	Intermediate Similarity	NPC133596
0.8082	Intermediate Similarity	NPC474574
0.8082	Intermediate Similarity	NPC128951
0.8082	Intermediate Similarity	NPC317913
0.8082	Intermediate Similarity	NPC192046
0.806	Intermediate Similarity	NPC477603
0.806	Intermediate Similarity	NPC472946
0.8056	Intermediate Similarity	NPC125767
0.8056	Intermediate Similarity	NPC200243
0.8056	Intermediate Similarity	NPC103822
0.8056	Intermediate Similarity	NPC21220
0.8028	Intermediate Similarity	NPC68426
0.8028	Intermediate Similarity	NPC195489
0.8028	Intermediate Similarity	NPC211009
0.8028	Intermediate Similarity	NPC477229
0.8028	Intermediate Similarity	NPC282905
0.8026	Intermediate Similarity	NPC289486
0.8026	Intermediate Similarity	NPC30583
0.8026	Intermediate Similarity	NPC61107
0.8026	Intermediate Similarity	NPC268040
0.8	Intermediate Similarity	NPC261616
0.7973	Intermediate Similarity	NPC31828
0.7973	Intermediate Similarity	NPC18857
0.7973	Intermediate Similarity	NPC477819
0.7973	Intermediate Similarity	NPC171426
0.7973	Intermediate Similarity	NPC244385
0.7973	Intermediate Similarity	NPC34046

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 NPC142712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	4435
0.2-0.3	3152
0.3-0.4	677
0.4-0.5	203
0.5-0.6	195
0.6-0.7	64
0.7-0.8	23
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
0.8939	High Similarity	NPD4267	Clinical (unspecified phase)
0.8529	High Similarity	NPD4787	Phase 1
0.8406	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6117	Approved
0.8169	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6116	Phase 1
0.7973	Intermediate Similarity	NPD6115	Approved
0.7973	Intermediate Similarity	NPD6114	Approved
0.7973	Intermediate Similarity	NPD6118	Approved
0.7973	Intermediate Similarity	NPD6697	Approved
0.7808	Intermediate Similarity	NPD3703	Phase 2
0.7763	Intermediate Similarity	NPD6928	Phase 2
0.7763	Intermediate Similarity	NPD7525	Registered
0.7746	Intermediate Similarity	NPD4245	Approved
0.7746	Intermediate Similarity	NPD4244	Approved
0.7746	Intermediate Similarity	NPD4789	Approved
0.7722	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5360	Phase 3
0.7714	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3698	Phase 2
0.7536	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7645	Phase 2
0.7333	Intermediate Similarity	NPD6942	Approved
0.7333	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD3671	Phase 1
0.7222	Intermediate Similarity	NPD6705	Phase 1
0.7162	Intermediate Similarity	NPD4758	Discontinued
0.7049	Intermediate Similarity	NPD385	Approved
0.7049	Intermediate Similarity	NPD384	Approved
0.7013	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8034	Phase 2
0.6977	Remote Similarity	NPD8035	Phase 2
0.6944	Remote Similarity	NPD4224	Phase 2
0.6933	Remote Similarity	NPD6081	Approved
0.6875	Remote Similarity	NPD4748	Discontinued
0.686	Remote Similarity	NPD6700	Approved
0.686	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5364	Discontinued
0.6782	Remote Similarity	NPD6702	Approved
0.6782	Remote Similarity	NPD6703	Approved
0.6753	Remote Similarity	NPD6924	Approved
0.6753	Remote Similarity	NPD6926	Approved
0.6747	Remote Similarity	NPD4786	Approved
0.6744	Remote Similarity	NPD5328	Approved
0.6711	Remote Similarity	NPD5777	Approved
0.6705	Remote Similarity	NPD8171	Discontinued
0.6667	Remote Similarity	NPD3702	Approved
0.6627	Remote Similarity	NPD4788	Approved
0.6591	Remote Similarity	NPD6079	Approved
0.6588	Remote Similarity	NPD3618	Phase 1
0.6582	Remote Similarity	NPD6933	Approved
0.6506	Remote Similarity	NPD3667	Approved
0.6494	Remote Similarity	NPD7151	Approved
0.6494	Remote Similarity	NPD4243	Approved
0.6494	Remote Similarity	NPD7150	Approved
0.6494	Remote Similarity	NPD7152	Approved
0.6447	Remote Similarity	NPD6923	Approved
0.6447	Remote Similarity	NPD6922	Approved
0.6413	Remote Similarity	NPD7920	Phase 3
0.6413	Remote Similarity	NPD7919	Phase 3
0.6404	Remote Similarity	NPD7515	Phase 2
0.6395	Remote Similarity	NPD8308	Discontinued
0.6374	Remote Similarity	NPD7991	Discontinued
0.6364	Remote Similarity	NPD7143	Approved
0.6364	Remote Similarity	NPD7144	Approved
0.6344	Remote Similarity	NPD8088	Phase 1
0.6341	Remote Similarity	NPD6929	Approved
0.6333	Remote Similarity	NPD4202	Approved
0.6329	Remote Similarity	NPD4784	Approved
0.6329	Remote Similarity	NPD4785	Approved
0.6322	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8418	Phase 2
0.6265	Remote Similarity	NPD6930	Phase 2
0.6265	Remote Similarity	NPD7509	Discontinued
0.6265	Remote Similarity	NPD6931	Approved
0.6216	Remote Similarity	NPD371	Approved
0.617	Remote Similarity	NPD7638	Approved
0.6163	Remote Similarity	NPD3133	Approved
0.6163	Remote Similarity	NPD3665	Phase 1
0.6163	Remote Similarity	NPD3666	Approved
0.6129	Remote Similarity	NPD5221	Approved
0.6129	Remote Similarity	NPD4697	Phase 3
0.6129	Remote Similarity	NPD5222	Approved
0.6129	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7639	Approved
0.6105	Remote Similarity	NPD7640	Approved
0.6098	Remote Similarity	NPD5776	Phase 2
0.6098	Remote Similarity	NPD6932	Approved
0.6098	Remote Similarity	NPD6925	Approved
0.6094	Remote Similarity	NPD388	Approved
0.6094	Remote Similarity	NPD386	Approved
0.6087	Remote Similarity	NPD7748	Approved
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD5173	Approved
0.6049	Remote Similarity	NPD4190	Phase 3
0.6049	Remote Similarity	NPD5275	Approved
0.6047	Remote Similarity	NPD6695	Phase 3
0.6024	Remote Similarity	NPD7145	Approved
0.602	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7632	Discontinued
0.5978	Remote Similarity	NPD6399	Phase 3
0.5977	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6920	Discontinued
0.5952	Remote Similarity	NPD4195	Approved
0.5952	Remote Similarity	NPD6683	Phase 2
0.5938	Remote Similarity	NPD5285	Approved
0.5938	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD5286	Approved
0.5938	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD6893	Approved
0.5895	Remote Similarity	NPD7902	Approved
0.589	Remote Similarity	NPD3198	Approved
0.5882	Remote Similarity	NPD7514	Phase 3
0.5876	Remote Similarity	NPD5223	Approved
0.5843	Remote Similarity	NPD5279	Phase 3
0.5842	Remote Similarity	NPD6415	Discontinued
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5290	Discontinued
0.5833	Remote Similarity	NPD3617	Approved
0.5824	Remote Similarity	NPD4753	Phase 2
0.5816	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD5225	Approved
0.5816	Remote Similarity	NPD5226	Approved
0.5816	Remote Similarity	NPD5224	Approved
0.5816	Remote Similarity	NPD4633	Approved
0.5814	Remote Similarity	NPD6902	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5795	Remote Similarity	NPD3668	Phase 3
0.5778	Remote Similarity	NPD7750	Discontinued
0.5778	Remote Similarity	NPD7524	Approved
0.5758	Remote Similarity	NPD4754	Approved
0.5758	Remote Similarity	NPD5175	Approved
0.5758	Remote Similarity	NPD5174	Approved
0.5747	Remote Similarity	NPD4223	Phase 3
0.5747	Remote Similarity	NPD4221	Approved
0.5743	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD1811	Approved
0.5732	Remote Similarity	NPD1810	Approved
0.573	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4159	Approved
0.57	Remote Similarity	NPD5141	Approved
0.5698	Remote Similarity	NPD7332	Phase 2
0.5694	Remote Similarity	NPD586	Phase 1
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD7320	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.5667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD8264	Approved
0.5644	Remote Similarity	NPD4767	Approved
0.5644	Remote Similarity	NPD4768	Approved
0.5632	Remote Similarity	NPD4692	Approved
0.5632	Remote Similarity	NPD6898	Phase 1
0.5632	Remote Similarity	NPD4139	Approved
0.5631	Remote Similarity	NPD6372	Approved
0.5631	Remote Similarity	NPD6373	Approved
0.5618	Remote Similarity	NPD4197	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