NPASS Compound

Structure

NPC187785 OpenBabel07101719132D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.8425 -4.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4316 -3.7831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0443 2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 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 1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 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 20 1 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 27 1 6 0 0 0 19 22 1 0 0 0 0 19 31 1 6 0 0 0 20 26 1 0 0 0 0 20 30 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 21 32 1 6 0 0 0 22 29 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 30 1 1 0 0 0 24 34 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 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	5.203
LogD:	4.453
LogS:	-4.048
# Rotatable Bonds:	0
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	5.248
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.832
MDCK Permeability:	1.5237234038067982e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.525
30% Bioavailability (F30%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	93.09921264648438%
Volume Distribution (VD):	1.516
Pgp-substrate:	4.163468837738037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.293
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.259
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	3.461
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.776
Maximum Recommended Daily Dose:	0.601
Skin Sensitization:	0.124
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC187785

Natural Product ID:	NPC187785
*Common Name:**	1Beta,2Alpha,3Beta,11Alpha-Tetrahydroxyolean-12-Ene
IUPAC Name:	(1S,2S,3R,4aS,6aR,6bS,8aR,12aR,14R,14aS,14bS)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-1,2,3,14-tetrol
Synonyms:
Standard InCHIKey:	RLHPTCMHCBNJKU-JCAJVAELSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-25(2)11-12-27(5)13-14-28(6)17(18(27)16-25)15-19(31)22-29(28,7)10-9-20-26(3,4)23(33)21(32)24(34)30(20,22)8/h15,18-24,31-34H,9-14,16H2,1-8H3/t18-,19+,20-,21-,22-,23-,24+,27+,28+,29+,30-/m0/s1
SMILES:	CC1(C)CC[C@]2(C)CC[C@]3(C)C(=C[C@H]([C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@H]([C@@H]([C@H]([C@]43C)O)O)O)O)[C@@H]2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472225
PubChem CID:	21670086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO23829	Salvia kronenburgii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738403]
NPO23829	Salvia kronenburgii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	27.9	ug.mL-1	PMID[505154]

☑ 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 NPC187785 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	229
0.1-0.2	1793
0.2-0.3	5357
0.3-0.4	13191
0.4-0.5	11011
0.5-0.6	5316
0.6-0.7	4022
0.7-0.8	1571
0.8-0.85	155
0.85-0.9	42
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259875
0.9405	High Similarity	NPC237344
0.9277	High Similarity	NPC159168
0.9277	High Similarity	NPC253402
0.9167	High Similarity	NPC238992
0.9157	High Similarity	NPC47763
0.907	High Similarity	NPC470620
0.9036	High Similarity	NPC242350
0.8925	High Similarity	NPC235920
0.8925	High Similarity	NPC96784
0.8916	High Similarity	NPC295131
0.8675	High Similarity	NPC253807
0.8675	High Similarity	NPC300499
0.8675	High Similarity	NPC196753
0.8675	High Similarity	NPC98386
0.8675	High Similarity	NPC158662
0.8675	High Similarity	NPC230295
0.8667	High Similarity	NPC41554
0.8667	High Similarity	NPC97404
0.8652	High Similarity	NPC470361
0.8588	High Similarity	NPC249423
0.8588	High Similarity	NPC476646
0.8571	High Similarity	NPC53744
0.8556	High Similarity	NPC329596
0.8556	High Similarity	NPC80561
0.8556	High Similarity	NPC3345
0.8556	High Similarity	NPC291484
0.8556	High Similarity	NPC11216
0.8556	High Similarity	NPC204188
0.8554	High Similarity	NPC34177
0.8554	High Similarity	NPC101475
0.8554	High Similarity	NPC157996
0.8554	High Similarity	NPC40394
0.8554	High Similarity	NPC130136
0.8539	High Similarity	NPC474668
0.8539	High Similarity	NPC133588
0.8511	High Similarity	NPC477876
0.8511	High Similarity	NPC477875
0.8495	Intermediate Similarity	NPC19376
0.8495	Intermediate Similarity	NPC305464
0.8495	Intermediate Similarity	NPC307282
0.8495	Intermediate Similarity	NPC25848
0.8488	Intermediate Similarity	NPC304285
0.8471	Intermediate Similarity	NPC96362
0.8471	Intermediate Similarity	NPC287749
0.8462	Intermediate Similarity	NPC275671
0.8452	Intermediate Similarity	NPC474989
0.8452	Intermediate Similarity	NPC22955
0.8452	Intermediate Similarity	NPC99168
0.8452	Intermediate Similarity	NPC470396
0.8444	Intermediate Similarity	NPC105495
0.8434	Intermediate Similarity	NPC290598
0.8434	Intermediate Similarity	NPC120098
0.8434	Intermediate Similarity	NPC265328
0.8434	Intermediate Similarity	NPC30590
0.8434	Intermediate Similarity	NPC27765
0.8434	Intermediate Similarity	NPC122418
0.837	Intermediate Similarity	NPC119379
0.8353	Intermediate Similarity	NPC291379
0.8351	Intermediate Similarity	NPC162354
0.8333	Intermediate Similarity	NPC477924
0.8333	Intermediate Similarity	NPC470711
0.8333	Intermediate Similarity	NPC256247
0.8333	Intermediate Similarity	NPC67872
0.8333	Intermediate Similarity	NPC470758
0.8316	Intermediate Similarity	NPC247233
0.8315	Intermediate Similarity	NPC299068
0.8315	Intermediate Similarity	NPC6391
0.8315	Intermediate Similarity	NPC71520
0.8315	Intermediate Similarity	NPC269058
0.8313	Intermediate Similarity	NPC138374
0.8313	Intermediate Similarity	NPC34700
0.8298	Intermediate Similarity	NPC288970
0.8295	Intermediate Similarity	NPC185568
0.828	Intermediate Similarity	NPC299996
0.828	Intermediate Similarity	NPC88116
0.828	Intermediate Similarity	NPC282395
0.828	Intermediate Similarity	NPC20235
0.828	Intermediate Similarity	NPC145667
0.828	Intermediate Similarity	NPC231063
0.828	Intermediate Similarity	NPC32407
0.828	Intermediate Similarity	NPC263548
0.828	Intermediate Similarity	NPC477605
0.8256	Intermediate Similarity	NPC471266
0.8256	Intermediate Similarity	NPC95124
0.8242	Intermediate Similarity	NPC109744
0.8235	Intermediate Similarity	NPC83351
0.8235	Intermediate Similarity	NPC167891
0.8229	Intermediate Similarity	NPC474190
0.8229	Intermediate Similarity	NPC476195
0.8229	Intermediate Similarity	NPC473790
0.8229	Intermediate Similarity	NPC474571
0.8229	Intermediate Similarity	NPC254567
0.8222	Intermediate Similarity	NPC186145
0.8222	Intermediate Similarity	NPC474657
0.8214	Intermediate Similarity	NPC470749
0.8214	Intermediate Similarity	NPC274079
0.8214	Intermediate Similarity	NPC477925
0.8214	Intermediate Similarity	NPC253190
0.8214	Intermediate Similarity	NPC106364
0.8211	Intermediate Similarity	NPC43686
0.8211	Intermediate Similarity	NPC477226
0.8211	Intermediate Similarity	NPC476893
0.8202	Intermediate Similarity	NPC470360
0.8193	Intermediate Similarity	NPC100334
0.8193	Intermediate Similarity	NPC306727
0.8182	Intermediate Similarity	NPC207013
0.8182	Intermediate Similarity	NPC85095
0.8182	Intermediate Similarity	NPC317458
0.8182	Intermediate Similarity	NPC237795
0.8182	Intermediate Similarity	NPC211135
0.8182	Intermediate Similarity	NPC88349
0.8182	Intermediate Similarity	NPC216420
0.8182	Intermediate Similarity	NPC82538
0.8172	Intermediate Similarity	NPC310013
0.8163	Intermediate Similarity	NPC473124
0.8163	Intermediate Similarity	NPC473123
0.8161	Intermediate Similarity	NPC471270
0.8152	Intermediate Similarity	NPC92885
0.8152	Intermediate Similarity	NPC473956
0.8152	Intermediate Similarity	NPC77796
0.8152	Intermediate Similarity	NPC476226
0.8152	Intermediate Similarity	NPC475751
0.8144	Intermediate Similarity	NPC476132
0.8132	Intermediate Similarity	NPC475664
0.8132	Intermediate Similarity	NPC280556
0.8125	Intermediate Similarity	NPC476895
0.8118	Intermediate Similarity	NPC90979
0.8118	Intermediate Similarity	NPC471798
0.8118	Intermediate Similarity	NPC472805
0.8118	Intermediate Similarity	NPC91594
0.8111	Intermediate Similarity	NPC24277
0.8111	Intermediate Similarity	NPC201273
0.8111	Intermediate Similarity	NPC261266
0.8111	Intermediate Similarity	NPC139724
0.8105	Intermediate Similarity	NPC210717
0.8105	Intermediate Similarity	NPC103165
0.8105	Intermediate Similarity	NPC204961
0.8105	Intermediate Similarity	NPC173744
0.8105	Intermediate Similarity	NPC73004
0.8105	Intermediate Similarity	NPC201657
0.81	Intermediate Similarity	NPC473586
0.8095	Intermediate Similarity	NPC32832
0.8095	Intermediate Similarity	NPC66566
0.8095	Intermediate Similarity	NPC144075
0.8095	Intermediate Similarity	NPC477923
0.809	Intermediate Similarity	NPC83702
0.8085	Intermediate Similarity	NPC87095
0.8085	Intermediate Similarity	NPC127718
0.8085	Intermediate Similarity	NPC159365
0.8085	Intermediate Similarity	NPC65402
0.8081	Intermediate Similarity	NPC203354
0.8081	Intermediate Similarity	NPC110656
0.8081	Intermediate Similarity	NPC473127
0.8081	Intermediate Similarity	NPC474281
0.8068	Intermediate Similarity	NPC248886
0.8068	Intermediate Similarity	NPC30166
0.8068	Intermediate Similarity	NPC101462
0.8065	Intermediate Similarity	NPC71074
0.8065	Intermediate Similarity	NPC235884
0.8065	Intermediate Similarity	NPC475708
0.8065	Intermediate Similarity	NPC52021
0.8065	Intermediate Similarity	NPC472149
0.8065	Intermediate Similarity	NPC84319
0.8065	Intermediate Similarity	NPC300351
0.8065	Intermediate Similarity	NPC25299
0.8065	Intermediate Similarity	NPC306541
0.8061	Intermediate Similarity	NPC283343
0.8061	Intermediate Similarity	NPC273668
0.8061	Intermediate Similarity	NPC258547
0.8046	Intermediate Similarity	NPC475679
0.8046	Intermediate Similarity	NPC236112
0.8046	Intermediate Similarity	NPC236707
0.8043	Intermediate Similarity	NPC101886
0.8023	Intermediate Similarity	NPC11908
0.8023	Intermediate Similarity	NPC72507
0.8022	Intermediate Similarity	NPC189777
0.8022	Intermediate Similarity	NPC476948
0.8021	Intermediate Similarity	NPC261935
0.8021	Intermediate Similarity	NPC9613
0.8021	Intermediate Similarity	NPC247139
0.8021	Intermediate Similarity	NPC189880
0.8021	Intermediate Similarity	NPC240372
0.8021	Intermediate Similarity	NPC106112
0.802	Intermediate Similarity	NPC475263
0.8	Intermediate Similarity	NPC80566
0.8	Intermediate Similarity	NPC96916
0.8	Intermediate Similarity	NPC476894
0.8	Intermediate Similarity	NPC8774
0.8	Intermediate Similarity	NPC32118
0.8	Intermediate Similarity	NPC477877
0.7979	Intermediate Similarity	NPC307335
0.7979	Intermediate Similarity	NPC74855
0.7979	Intermediate Similarity	NPC136313
0.7979	Intermediate Similarity	NPC275809
0.7978	Intermediate Similarity	NPC110778
0.7978	Intermediate Similarity	NPC113978
0.7978	Intermediate Similarity	NPC474634
0.7978	Intermediate Similarity	NPC185605
0.7976	Intermediate Similarity	NPC91858

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 NPC187785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2040
0.2-0.3	4003
0.3-0.4	2016
0.4-0.5	538
0.5-0.6	227
0.6-0.7	108
0.7-0.8	7
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7645	Phase 2
0.7841	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD7515	Phase 2
0.7447	Intermediate Similarity	NPD7524	Approved
0.7333	Intermediate Similarity	NPD6929	Approved
0.7312	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7263	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6931	Approved
0.7253	Intermediate Similarity	NPD6930	Phase 2
0.7204	Intermediate Similarity	NPD6695	Phase 3
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7748	Approved
0.7157	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7639	Approved
0.7129	Intermediate Similarity	NPD7902	Approved
0.7111	Intermediate Similarity	NPD6925	Approved
0.7111	Intermediate Similarity	NPD5776	Phase 2
0.7079	Intermediate Similarity	NPD8264	Approved
0.7065	Intermediate Similarity	NPD7332	Phase 2
0.7065	Intermediate Similarity	NPD7514	Phase 3
0.7059	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD7145	Approved
0.6991	Remote Similarity	NPD7516	Approved
0.6989	Remote Similarity	NPD6902	Approved
0.6907	Remote Similarity	NPD7750	Discontinued
0.6903	Remote Similarity	NPD7327	Approved
0.6903	Remote Similarity	NPD7328	Approved
0.6875	Remote Similarity	NPD6893	Approved
0.687	Remote Similarity	NPD8379	Approved
0.687	Remote Similarity	NPD8378	Approved
0.687	Remote Similarity	NPD8296	Approved
0.687	Remote Similarity	NPD8380	Approved
0.687	Remote Similarity	NPD8335	Approved
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6813	Remote Similarity	NPD6933	Approved
0.6809	Remote Similarity	NPD6898	Phase 1
0.6804	Remote Similarity	NPD3618	Phase 1
0.6789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8294	Approved
0.6783	Remote Similarity	NPD8377	Approved
0.6771	Remote Similarity	NPD4786	Approved
0.6768	Remote Similarity	NPD5328	Approved
0.6762	Remote Similarity	NPD5344	Discontinued
0.6739	Remote Similarity	NPD6932	Approved
0.6737	Remote Similarity	NPD3667	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6724	Remote Similarity	NPD8033	Approved
0.6705	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD368	Approved
0.6635	Remote Similarity	NPD4755	Approved
0.6634	Remote Similarity	NPD6079	Approved
0.6634	Remote Similarity	NPD7087	Discontinued
0.661	Remote Similarity	NPD8328	Phase 3
0.6606	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD4159	Approved
0.6596	Remote Similarity	NPD6683	Phase 2
0.6593	Remote Similarity	NPD6926	Approved
0.6593	Remote Similarity	NPD6924	Approved
0.6581	Remote Similarity	NPD7503	Approved
0.6577	Remote Similarity	NPD4634	Approved
0.6574	Remote Similarity	NPD5141	Approved
0.6569	Remote Similarity	NPD4202	Approved
0.6556	Remote Similarity	NPD4243	Approved
0.6542	Remote Similarity	NPD7632	Discontinued
0.6526	Remote Similarity	NPD7509	Discontinued
0.6522	Remote Similarity	NPD7115	Discovery
0.6522	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5285	Approved
0.6509	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD4700	Approved
0.6509	Remote Similarity	NPD4696	Approved
0.6489	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD3133	Approved
0.6429	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4785	Approved
0.6413	Remote Similarity	NPD4784	Approved
0.6408	Remote Similarity	NPD6399	Phase 3
0.6396	Remote Similarity	NPD6686	Approved
0.6396	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5225	Approved
0.6389	Remote Similarity	NPD5226	Approved
0.6389	Remote Similarity	NPD5224	Approved
0.6389	Remote Similarity	NPD4633	Approved
0.6381	Remote Similarity	NPD5222	Approved
0.6381	Remote Similarity	NPD5221	Approved
0.6381	Remote Similarity	NPD4697	Phase 3
0.6381	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7151	Approved
0.6374	Remote Similarity	NPD7150	Approved
0.6374	Remote Similarity	NPD7152	Approved
0.6373	Remote Similarity	NPD7136	Phase 2
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6355	Remote Similarity	NPD6648	Approved
0.6354	Remote Similarity	NPD4748	Discontinued
0.6348	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7319	Approved
0.6333	Remote Similarity	NPD6923	Approved
0.6333	Remote Similarity	NPD6922	Approved
0.633	Remote Similarity	NPD5174	Approved
0.633	Remote Similarity	NPD5175	Approved
0.6321	Remote Similarity	NPD5173	Approved
0.6296	Remote Similarity	NPD5223	Approved
0.6275	Remote Similarity	NPD4753	Phase 2
0.6264	Remote Similarity	NPD7144	Approved
0.6264	Remote Similarity	NPD7143	Approved
0.6263	Remote Similarity	NPD3668	Phase 3
0.6261	Remote Similarity	NPD4632	Approved
0.6261	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6216	Remote Similarity	NPD4768	Approved
0.6216	Remote Similarity	NPD4767	Approved
0.6216	Remote Similarity	NPD6640	Phase 3
0.6214	Remote Similarity	NPD3168	Discontinued
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD4754	Approved
0.6174	Remote Similarity	NPD8297	Approved
0.617	Remote Similarity	NPD4190	Phase 3
0.617	Remote Similarity	NPD5275	Approved
0.6161	Remote Similarity	NPD5697	Approved
0.6161	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5701	Approved
0.6145	Remote Similarity	NPD342	Phase 1
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD4623	Approved
0.6139	Remote Similarity	NPD4519	Discontinued
0.6136	Remote Similarity	NPD371	Approved
0.6129	Remote Similarity	NPD4732	Discontinued
0.6117	Remote Similarity	NPD6051	Approved
0.6117	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5290	Discontinued
0.6106	Remote Similarity	NPD4729	Approved
0.6106	Remote Similarity	NPD4730	Approved
0.6106	Remote Similarity	NPD5128	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6087	Remote Similarity	NPD6650	Approved
0.6083	Remote Similarity	NPD6319	Approved
0.6083	Remote Similarity	NPD6059	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6082	Remote Similarity	NPD4195	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.6034	Remote Similarity	NPD6882	Approved
0.602	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD5251	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD5247	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5981	Remote Similarity	NPD5210	Approved
0.5981	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD5279	Phase 3
0.598	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6697	Approved
0.5979	Remote Similarity	NPD6118	Approved
0.5979	Remote Similarity	NPD6114	Approved
0.5979	Remote Similarity	NPD6115	Approved
0.5966	Remote Similarity	NPD6009	Approved
0.5965	Remote Similarity	NPD6011	Approved
0.5948	Remote Similarity	NPD5215	Approved
0.5948	Remote Similarity	NPD5216	Approved
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5217	Approved
0.5943	Remote Similarity	NPD8171	Discontinued
0.5902	Remote Similarity	NPD8516	Approved
0.5902	Remote Similarity	NPD8517	Approved
0.5902	Remote Similarity	NPD8515	Approved
0.5902	Remote Similarity	NPD8513	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