NPASS Compound

Structure

CID231680 OpenBabel06191716032D 33 37 0 0 1 0 0 0 0 0999 V2000 -7.7749 1.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2880 0.7174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4017 -0.1754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5342 0.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 2.0475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3966 -0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 -1.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9179 0.6247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5850 1.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4282 1.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2575 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9579 0.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9579 3.0212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0825 -1.5733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 2.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2258 -1.3391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 -0.3867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8581 -1.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5850 0.1001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8614 -0.5514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9579 1.0738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2715 1.0738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8012 2.5344 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6128 -0.7567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8012 1.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5851 -0.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 1.5607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4282 -0.3867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2715 0.1001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9090 -0.3489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6444 3.0212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1154 -1.5223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 11 1 1 0 0 0 20 30 1 0 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 6 0 0 0 24 33 1 0 0 0 0 26 32 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	511.024
LogP:	5.89
LogD:	5.025
LogS:	-5.027
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	4.776
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:	-4.973
MDCK Permeability:	2.7939368010265753e-05
Pgp-inhibitor:	0.773
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.562

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	94.99124908447266%
Volume Distribution (VD):	1.097
Pgp-substrate:	2.049234390258789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.362
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	3.526
Half-life (T1/2):	0.089

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.934
Carcinogencity:	0.006
Eye Corrosion:	0.976
Eye Irritation:	0.615
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC231680

Natural Product ID:	NPC231680
*Common Name:**	Cabraleadiol
IUPAC Name:	(3R,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,5S)-5-(2-hydroxypropan-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-3-ol
Synonyms:
Standard InCHIKey:	RQBNSDSKUAGBOI-ZNYSIYOKSA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-25(2)21-12-17-29(7)22(27(21,5)15-13-23(25)31)10-9-19-20(11-16-28(19,29)6)30(8)18-14-24(33-30)26(3,4)32/h19-24,31-32H,9-18H2,1-8H3/t19-,20+,21+,22-,23-,24+,27+,28-,29-,30+/m1/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CC[C@@H](C(C)(C)O)O3)[C@@]2(C)CC[C@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109461
PubChem CID:	21625899
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
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21087017]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21087017]
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7856	Streptomyces halstedii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2480	Amoora rohituka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2633	Baccharis minutiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9750	Dysoxylum malabaricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4668	Sideritis flavovirens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4372	Halimium halimifolium	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7674	Tragopogon orientalis	Species	Asteraceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[469177]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[469177]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[469177]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[469177]

☑ 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 NPC231680 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	398
0.1-0.2	4111
0.2-0.3	15180
0.3-0.4	10034
0.4-0.5	5201
0.5-0.6	4630
0.6-0.7	2291
0.7-0.8	709
0.8-0.85	84
0.85-0.9	45
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91387
1.0	High Similarity	NPC270306
0.9718	High Similarity	NPC133596
0.9718	High Similarity	NPC64081
0.9718	High Similarity	NPC474574
0.9718	High Similarity	NPC11907
0.9452	High Similarity	NPC81074
0.9452	High Similarity	NPC477282
0.9079	High Similarity	NPC475388
0.9014	High Similarity	NPC157777
0.9014	High Similarity	NPC131506
0.8961	High Similarity	NPC477285
0.8961	High Similarity	NPC111582
0.8961	High Similarity	NPC470070
0.8947	High Similarity	NPC190940
0.8889	High Similarity	NPC473238
0.8889	High Similarity	NPC153719
0.8889	High Similarity	NPC472341
0.8831	High Similarity	NPC477286
0.8831	High Similarity	NPC286719
0.8816	High Similarity	NPC16449
0.8784	High Similarity	NPC470145
0.8767	High Similarity	NPC228994
0.8767	High Similarity	NPC10476
0.8767	High Similarity	NPC192501
0.875	High Similarity	NPC187471
0.875	High Similarity	NPC1340
0.875	High Similarity	NPC127283
0.875	High Similarity	NPC252182
0.875	High Similarity	NPC8004
0.875	High Similarity	NPC470071
0.8732	High Similarity	NPC107919
0.8732	High Similarity	NPC254037
0.8732	High Similarity	NPC470830
0.8732	High Similarity	NPC299948
0.8732	High Similarity	NPC129829
0.8732	High Similarity	NPC66407
0.8732	High Similarity	NPC241085
0.8649	High Similarity	NPC196136
0.8649	High Similarity	NPC158208
0.8649	High Similarity	NPC317242
0.8649	High Similarity	NPC243027
0.863	High Similarity	NPC470610
0.8625	High Similarity	NPC215968
0.8625	High Similarity	NPC80700
0.8625	High Similarity	NPC155531
0.8611	High Similarity	NPC231945
0.8611	High Similarity	NPC282454
0.8611	High Similarity	NPC192192
0.8608	High Similarity	NPC320824
0.859	High Similarity	NPC470611
0.8533	High Similarity	NPC163597
0.8519	High Similarity	NPC210658
0.8519	High Similarity	NPC161928
0.8514	High Similarity	NPC48795
0.8493	Intermediate Similarity	NPC127094
0.8493	Intermediate Similarity	NPC473279
0.8493	Intermediate Similarity	NPC109457
0.8493	Intermediate Similarity	NPC100586
0.8493	Intermediate Similarity	NPC195530
0.8493	Intermediate Similarity	NPC157422
0.8472	Intermediate Similarity	NPC477820
0.8451	Intermediate Similarity	NPC48079
0.8451	Intermediate Similarity	NPC63190
0.8442	Intermediate Similarity	NPC31302
0.8442	Intermediate Similarity	NPC245029
0.8421	Intermediate Similarity	NPC192046
0.8421	Intermediate Similarity	NPC128951
0.8421	Intermediate Similarity	NPC476233
0.8421	Intermediate Similarity	NPC185915
0.8421	Intermediate Similarity	NPC477227
0.8421	Intermediate Similarity	NPC105208
0.8421	Intermediate Similarity	NPC302578
0.8415	Intermediate Similarity	NPC473436
0.8415	Intermediate Similarity	NPC128475
0.8406	Intermediate Similarity	NPC114891
0.84	Intermediate Similarity	NPC472950
0.84	Intermediate Similarity	NPC472952
0.8395	Intermediate Similarity	NPC103782
0.8395	Intermediate Similarity	NPC477283
0.8395	Intermediate Similarity	NPC114378
0.8356	Intermediate Similarity	NPC232925
0.8356	Intermediate Similarity	NPC63588
0.8356	Intermediate Similarity	NPC251201
0.8354	Intermediate Similarity	NPC154043
0.8354	Intermediate Similarity	NPC60018
0.8354	Intermediate Similarity	NPC202688
0.8333	Intermediate Similarity	NPC472741
0.8313	Intermediate Similarity	NPC82955
0.8313	Intermediate Similarity	NPC228059
0.8312	Intermediate Similarity	NPC67657
0.8312	Intermediate Similarity	NPC471769
0.8312	Intermediate Similarity	NPC18857
0.8312	Intermediate Similarity	NPC147993
0.831	Intermediate Similarity	NPC142712
0.8289	Intermediate Similarity	NPC477602
0.8289	Intermediate Similarity	NPC473916
0.8289	Intermediate Similarity	NPC477601
0.8272	Intermediate Similarity	NPC273290
0.8272	Intermediate Similarity	NPC232044
0.8272	Intermediate Similarity	NPC290612
0.8267	Intermediate Similarity	NPC477508
0.8267	Intermediate Similarity	NPC304499
0.8261	Intermediate Similarity	NPC218585
0.8261	Intermediate Similarity	NPC148174
0.8261	Intermediate Similarity	NPC71460
0.825	Intermediate Similarity	NPC268578
0.825	Intermediate Similarity	NPC217559
0.825	Intermediate Similarity	NPC292458
0.8219	Intermediate Similarity	NPC470833
0.8205	Intermediate Similarity	NPC287452
0.8205	Intermediate Similarity	NPC220379
0.8205	Intermediate Similarity	NPC477287
0.8194	Intermediate Similarity	NPC473230
0.8194	Intermediate Similarity	NPC475884
0.8193	Intermediate Similarity	NPC56777
0.8193	Intermediate Similarity	NPC201607
0.8182	Intermediate Similarity	NPC212453
0.8182	Intermediate Similarity	NPC171658
0.8169	Intermediate Similarity	NPC260116
0.8169	Intermediate Similarity	NPC243469
0.8169	Intermediate Similarity	NPC473276
0.8169	Intermediate Similarity	NPC474380
0.8169	Intermediate Similarity	NPC41577
0.8169	Intermediate Similarity	NPC475943
0.8169	Intermediate Similarity	NPC190827
0.8148	Intermediate Similarity	NPC227260
0.8125	Intermediate Similarity	NPC296734
0.8118	Intermediate Similarity	NPC210759
0.8118	Intermediate Similarity	NPC473066
0.8118	Intermediate Similarity	NPC229801
0.8118	Intermediate Similarity	NPC307167
0.8101	Intermediate Similarity	NPC248944
0.8101	Intermediate Similarity	NPC7479
0.8101	Intermediate Similarity	NPC257296
0.8095	Intermediate Similarity	NPC20822
0.8082	Intermediate Similarity	NPC474756
0.8077	Intermediate Similarity	NPC471045
0.8072	Intermediate Similarity	NPC43912
0.8072	Intermediate Similarity	NPC140446
0.8056	Intermediate Similarity	NPC44122
0.8052	Intermediate Similarity	NPC91573
0.8049	Intermediate Similarity	NPC266651
0.8028	Intermediate Similarity	NPC281540
0.8028	Intermediate Similarity	NPC167995
0.8028	Intermediate Similarity	NPC118937
0.8028	Intermediate Similarity	NPC159654
0.8028	Intermediate Similarity	NPC69149
0.8026	Intermediate Similarity	NPC470151
0.8025	Intermediate Similarity	NPC132635
0.8023	Intermediate Similarity	NPC256104
0.8023	Intermediate Similarity	NPC211845
0.8023	Intermediate Similarity	NPC311246
0.8023	Intermediate Similarity	NPC167644
0.8023	Intermediate Similarity	NPC122083
0.8023	Intermediate Similarity	NPC182740
0.8	Intermediate Similarity	NPC58631
0.8	Intermediate Similarity	NPC473542
0.8	Intermediate Similarity	NPC73515
0.7975	Intermediate Similarity	NPC269333
0.7975	Intermediate Similarity	NPC476176
0.7952	Intermediate Similarity	NPC471240
0.7952	Intermediate Similarity	NPC474448
0.7931	Intermediate Similarity	NPC113500
0.7931	Intermediate Similarity	NPC30687
0.7931	Intermediate Similarity	NPC252253
0.7931	Intermediate Similarity	NPC477224
0.7931	Intermediate Similarity	NPC175
0.7931	Intermediate Similarity	NPC305418
0.7931	Intermediate Similarity	NPC45959
0.7931	Intermediate Similarity	NPC3538
0.7922	Intermediate Similarity	NPC186851
0.7917	Intermediate Similarity	NPC472946
0.7907	Intermediate Similarity	NPC5632
0.7907	Intermediate Similarity	NPC59006
0.7907	Intermediate Similarity	NPC149966
0.7901	Intermediate Similarity	NPC477284
0.7901	Intermediate Similarity	NPC242771
0.7901	Intermediate Similarity	NPC311642
0.7901	Intermediate Similarity	NPC164289
0.7901	Intermediate Similarity	NPC100366
0.7895	Intermediate Similarity	NPC253805
0.7887	Intermediate Similarity	NPC249078
0.7887	Intermediate Similarity	NPC236099
0.7887	Intermediate Similarity	NPC209686
0.7882	Intermediate Similarity	NPC131466
0.7875	Intermediate Similarity	NPC472951
0.7875	Intermediate Similarity	NPC472943
0.7857	Intermediate Similarity	NPC202937
0.7848	Intermediate Similarity	NPC31828
0.7841	Intermediate Similarity	NPC473064
0.7841	Intermediate Similarity	NPC473067
0.7841	Intermediate Similarity	NPC473065
0.7838	Intermediate Similarity	NPC475893
0.7826	Intermediate Similarity	NPC476735
0.7821	Intermediate Similarity	NPC107963
0.7816	Intermediate Similarity	NPC144790
0.7816	Intermediate Similarity	NPC88962
0.7816	Intermediate Similarity	NPC149400
0.7805	Intermediate Similarity	NPC211135

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 NPC231680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	4229
0.2-0.3	3202
0.3-0.4	738
0.4-0.5	255
0.5-0.6	233
0.6-0.7	57
0.7-0.8	18
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8732	High Similarity	NPD4267	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6928	Phase 2
0.7867	Intermediate Similarity	NPD4787	Phase 1
0.7625	Intermediate Similarity	NPD6697	Approved
0.7625	Intermediate Similarity	NPD6118	Approved
0.7625	Intermediate Similarity	NPD6114	Approved
0.7625	Intermediate Similarity	NPD6115	Approved
0.7614	Intermediate Similarity	NPD8171	Discontinued
0.7532	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3703	Phase 2
0.7375	Intermediate Similarity	NPD6117	Approved
0.7342	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD371	Approved
0.7284	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD5360	Phase 3
0.7143	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4245	Approved
0.6962	Remote Similarity	NPD4244	Approved
0.6962	Remote Similarity	NPD4789	Approved
0.6837	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3698	Phase 2
0.6753	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7991	Discontinued
0.6667	Remote Similarity	NPD4758	Discontinued
0.6667	Remote Similarity	NPD7524	Approved
0.663	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6700	Approved
0.6629	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6942	Approved
0.6627	Remote Similarity	NPD7339	Approved
0.6627	Remote Similarity	NPD3702	Approved
0.6588	Remote Similarity	NPD3671	Phase 1
0.6559	Remote Similarity	NPD6702	Approved
0.6559	Remote Similarity	NPD6703	Approved
0.6556	Remote Similarity	NPD8308	Discontinued
0.6548	Remote Similarity	NPD6933	Approved
0.6512	Remote Similarity	NPD7645	Phase 2
0.6506	Remote Similarity	NPD1811	Approved
0.6506	Remote Similarity	NPD1810	Approved
0.65	Remote Similarity	NPD6705	Phase 1
0.6463	Remote Similarity	NPD5777	Approved
0.6437	Remote Similarity	NPD4748	Discontinued
0.6404	Remote Similarity	NPD6695	Phase 3
0.6395	Remote Similarity	NPD5364	Discontinued
0.6383	Remote Similarity	NPD8034	Phase 2
0.6383	Remote Similarity	NPD8035	Phase 2
0.6353	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7638	Approved
0.631	Remote Similarity	NPD6926	Approved
0.631	Remote Similarity	NPD6924	Approved
0.6304	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6081	Approved
0.6263	Remote Similarity	NPD7639	Approved
0.6263	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD6930	Phase 2
0.625	Remote Similarity	NPD4224	Phase 2
0.6239	Remote Similarity	NPD7327	Approved
0.6239	Remote Similarity	NPD7328	Approved
0.6232	Remote Similarity	NPD384	Approved
0.6232	Remote Similarity	NPD385	Approved
0.6222	Remote Similarity	NPD4788	Approved
0.62	Remote Similarity	NPD4159	Approved
0.6182	Remote Similarity	NPD7516	Approved
0.617	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD4786	Approved
0.6145	Remote Similarity	NPD2686	Approved
0.6145	Remote Similarity	NPD2687	Approved
0.6145	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD2254	Approved
0.6139	Remote Similarity	NPD7632	Discontinued
0.6136	Remote Similarity	NPD6929	Approved
0.6129	Remote Similarity	NPD7750	Discontinued
0.6126	Remote Similarity	NPD8377	Approved
0.6126	Remote Similarity	NPD8294	Approved
0.61	Remote Similarity	NPD8418	Phase 2
0.6092	Remote Similarity	NPD6932	Approved
0.6087	Remote Similarity	NPD386	Approved
0.6087	Remote Similarity	NPD388	Approved
0.6071	Remote Similarity	NPD8296	Approved
0.6071	Remote Similarity	NPD4243	Approved
0.6071	Remote Similarity	NPD8335	Approved
0.6071	Remote Similarity	NPD8379	Approved
0.6071	Remote Similarity	NPD8033	Approved
0.6071	Remote Similarity	NPD8380	Approved
0.6071	Remote Similarity	NPD8378	Approved
0.6042	Remote Similarity	NPD6079	Approved
0.604	Remote Similarity	NPD1700	Approved
0.6022	Remote Similarity	NPD3618	Phase 1
0.6019	Remote Similarity	NPD8133	Approved
0.5982	Remote Similarity	NPD6059	Approved
0.5982	Remote Similarity	NPD6054	Approved
0.5979	Remote Similarity	NPD4202	Approved
0.5955	Remote Similarity	NPD6683	Phase 2
0.5934	Remote Similarity	NPD3667	Approved
0.593	Remote Similarity	NPD4785	Approved
0.593	Remote Similarity	NPD4784	Approved
0.5914	Remote Similarity	NPD6893	Approved
0.5909	Remote Similarity	NPD6940	Discontinued
0.5909	Remote Similarity	NPD5776	Phase 2
0.5909	Remote Similarity	NPD6925	Approved
0.59	Remote Similarity	NPD7920	Phase 3
0.59	Remote Similarity	NPD7919	Phase 3
0.5889	Remote Similarity	NPD7509	Discontinued
0.5889	Remote Similarity	NPD7514	Phase 3
0.5882	Remote Similarity	NPD7152	Approved
0.5882	Remote Similarity	NPD7151	Approved
0.5882	Remote Similarity	NPD7150	Approved
0.5877	Remote Similarity	NPD6370	Approved
0.5876	Remote Similarity	NPD7087	Discontinued
0.5872	Remote Similarity	NPD4632	Approved
0.587	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.587	Remote Similarity	NPD3669	Approved
0.5862	Remote Similarity	NPD7507	Approved
0.5849	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7320	Approved
0.5849	Remote Similarity	NPD8174	Phase 2
0.5843	Remote Similarity	NPD7145	Approved
0.5842	Remote Similarity	NPD8088	Phase 1
0.5833	Remote Similarity	NPD6922	Approved
0.5833	Remote Similarity	NPD6923	Approved
0.5816	Remote Similarity	NPD6399	Phase 3
0.581	Remote Similarity	NPD6920	Discontinued
0.581	Remote Similarity	NPD7128	Approved
0.581	Remote Similarity	NPD6402	Approved
0.581	Remote Similarity	NPD5739	Approved
0.581	Remote Similarity	NPD6675	Approved
0.5794	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6016	Approved
0.5789	Remote Similarity	NPD6015	Approved
0.578	Remote Similarity	NPD8297	Approved
0.5776	Remote Similarity	NPD7492	Approved
0.5765	Remote Similarity	NPD7143	Approved
0.5765	Remote Similarity	NPD7144	Approved
0.5763	Remote Similarity	NPD7736	Approved
0.5755	Remote Similarity	NPD6412	Phase 2
0.5743	Remote Similarity	NPD4755	Approved
0.5741	Remote Similarity	NPD4634	Approved
0.5739	Remote Similarity	NPD5988	Approved
0.5726	Remote Similarity	NPD6616	Approved
0.5714	Remote Similarity	NPD7332	Phase 2
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD7319	Approved
0.5702	Remote Similarity	NPD6319	Approved
0.5701	Remote Similarity	NPD6881	Approved
0.5701	Remote Similarity	NPD6899	Approved
0.5686	Remote Similarity	NPD4225	Approved
0.5682	Remote Similarity	NPD5275	Approved
0.5682	Remote Similarity	NPD4190	Phase 3
0.5678	Remote Similarity	NPD8293	Discontinued
0.5678	Remote Similarity	NPD7078	Approved
0.566	Remote Similarity	NPD6008	Approved
0.5652	Remote Similarity	NPD7503	Approved
0.5652	Remote Similarity	NPD6898	Phase 1
0.5652	Remote Similarity	NPD6902	Approved
0.5648	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6372	Approved
0.5648	Remote Similarity	NPD6373	Approved
0.5644	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4697	Phase 3
0.5644	Remote Similarity	NPD5221	Approved
0.5644	Remote Similarity	NPD5222	Approved
0.5638	Remote Similarity	NPD3665	Phase 1
0.5638	Remote Similarity	NPD3133	Approved
0.5638	Remote Similarity	NPD3666	Approved
0.5631	Remote Similarity	NPD4696	Approved
0.5631	Remote Similarity	NPD5285	Approved
0.5631	Remote Similarity	NPD4700	Approved
0.5631	Remote Similarity	NPD5286	Approved
0.563	Remote Similarity	NPD6033	Approved
0.5607	Remote Similarity	NPD5697	Approved
0.5607	Remote Similarity	NPD5701	Approved
0.5604	Remote Similarity	NPD4195	Approved
0.56	Remote Similarity	NPD7748	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