NPASS Compound

Structure

NPC474571 OpenBabel07101718192D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.0694 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 4.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 4.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0469 -2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0694 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3796 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 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 -1.6898 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9143 -1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 -1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 11 23 2 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 31 1 0 0 0 0 14 15 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 29 1 0 0 0 0 17 30 1 0 0 0 0 18 21 1 0 0 0 0 18 27 1 0 0 0 0 19 33 2 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 0 0 0 0 22 32 1 1 0 0 0 23 31 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 6 0 0 0 25 32 1 1 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 36 1 1 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	6.21
LogD:	4.817
LogS:	-6.003
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	5.216
Fsp3:	0.844
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:	-5.056
MDCK Permeability:	1.6501324353157543e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	98.31841278076172%
Volume Distribution (VD):	1.898
Pgp-substrate:	2.785651206970215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.308
CYP3A4-substrate:	0.826

ADMET: Excretion

Clearance (CL):	2.273
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.392
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.646
Maximum Recommended Daily Dose:	0.783
Skin Sensitization:	0.541
Carcinogencity:	0.187
Eye Corrosion:	0.016
Eye Irritation:	0.013
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC474571

Natural Product ID:	NPC474571
*Common Name:**	1Beta,2Alpha-Dihydroxy-3Beta-Acetoxyolean-9(11),12-Diene
IUPAC Name:	[(1S,2R,3R,4aS,6aS,6bR,8aR,12aR,14bS)-1,2-dihydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a-dodecahydropicen-3-yl] acetate
Synonyms:
Standard InCHIKey:	GFBKCMWKFKJJAQ-IJVUUCQASA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-19(33)36-26-24(34)25(35)32(9)22(28(26,4)5)12-13-31(8)23(32)11-10-20-21-18-27(2,3)14-15-29(21,6)16-17-30(20,31)7/h10-11,21-22,24-26,34-35H,12-18H2,1-9H3/t21-,22-,24+,25+,26-,29+,30+,31+,32-/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@]2([C@H](C1(C)C)CC[C@@]1(C2=CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474064
PubChem CID:	21594132
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	=	36.9	ug.mL-1	PMID[483364]

☑ 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 NPC474571 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	227
0.1-0.2	1444
0.2-0.3	4613
0.3-0.4	10074
0.4-0.5	13411
0.5-0.6	5678
0.6-0.7	4716
0.7-0.8	2055
0.8-0.85	422
0.85-0.9	47
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254567
0.9468	High Similarity	NPC477875
0.9468	High Similarity	NPC477876
0.9271	High Similarity	NPC235920
0.9271	High Similarity	NPC96784
0.9271	High Similarity	NPC476132
0.9247	High Similarity	NPC215700
0.9167	High Similarity	NPC476195
0.9062	High Similarity	NPC247233
0.89	High Similarity	NPC477877
0.8812	High Similarity	NPC473586
0.8763	High Similarity	NPC476879
0.8763	High Similarity	NPC476878
0.8725	High Similarity	NPC475263
0.8713	High Similarity	NPC88349
0.8687	High Similarity	NPC155974
0.8673	High Similarity	NPC102426
0.8673	High Similarity	NPC300179
0.866	High Similarity	NPC230151
0.8641	High Similarity	NPC310546
0.8614	High Similarity	NPC173583
0.8587	High Similarity	NPC191965
0.8586	High Similarity	NPC473790
0.8586	High Similarity	NPC474190
0.8586	High Similarity	NPC208358
0.8557	High Similarity	NPC474727
0.85	High Similarity	NPC256247
0.85	High Similarity	NPC54909
0.85	High Similarity	NPC289670
0.85	High Similarity	NPC233012
0.8495	Intermediate Similarity	NPC237344
0.8495	Intermediate Similarity	NPC137306
0.8495	Intermediate Similarity	NPC84121
0.8485	Intermediate Similarity	NPC470068
0.8469	Intermediate Similarity	NPC25848
0.8469	Intermediate Similarity	NPC307282
0.8469	Intermediate Similarity	NPC305464
0.8469	Intermediate Similarity	NPC19376
0.8454	Intermediate Similarity	NPC159365
0.8454	Intermediate Similarity	NPC296164
0.8416	Intermediate Similarity	NPC273668
0.8416	Intermediate Similarity	NPC283343
0.8416	Intermediate Similarity	NPC258547
0.8396	Intermediate Similarity	NPC64106
0.8396	Intermediate Similarity	NPC125923
0.8396	Intermediate Similarity	NPC116794
0.8396	Intermediate Similarity	NPC212968
0.8396	Intermediate Similarity	NPC65590
0.8384	Intermediate Similarity	NPC475032
0.8384	Intermediate Similarity	NPC475033
0.8384	Intermediate Similarity	NPC43686
0.8381	Intermediate Similarity	NPC476881
0.8381	Intermediate Similarity	NPC476880
0.8381	Intermediate Similarity	NPC476882
0.8381	Intermediate Similarity	NPC7870
0.8381	Intermediate Similarity	NPC476886
0.8381	Intermediate Similarity	NPC102914
0.8381	Intermediate Similarity	NPC476883
0.8381	Intermediate Similarity	NPC68419
0.8381	Intermediate Similarity	NPC110139
0.8381	Intermediate Similarity	NPC476884
0.8381	Intermediate Similarity	NPC476887
0.8381	Intermediate Similarity	NPC274507
0.8381	Intermediate Similarity	NPC476885
0.8381	Intermediate Similarity	NPC75747
0.8381	Intermediate Similarity	NPC199457
0.8381	Intermediate Similarity	NPC108709
0.837	Intermediate Similarity	NPC132386
0.8351	Intermediate Similarity	NPC307335
0.8351	Intermediate Similarity	NPC136313
0.8351	Intermediate Similarity	NPC86368
0.8351	Intermediate Similarity	NPC74855
0.8333	Intermediate Similarity	NPC473129
0.8333	Intermediate Similarity	NPC99627
0.8333	Intermediate Similarity	NPC474124
0.8318	Intermediate Similarity	NPC271138
0.8318	Intermediate Similarity	NPC269315
0.8317	Intermediate Similarity	NPC470054
0.8317	Intermediate Similarity	NPC473160
0.8317	Intermediate Similarity	NPC475617
0.8302	Intermediate Similarity	NPC473481
0.8302	Intermediate Similarity	NPC211798
0.8302	Intermediate Similarity	NPC297208
0.8302	Intermediate Similarity	NPC179434
0.8302	Intermediate Similarity	NPC30397
0.8302	Intermediate Similarity	NPC235841
0.8302	Intermediate Similarity	NPC108748
0.8302	Intermediate Similarity	NPC191763
0.8302	Intermediate Similarity	NPC190837
0.83	Intermediate Similarity	NPC470066
0.83	Intermediate Similarity	NPC470067
0.83	Intermediate Similarity	NPC260149
0.83	Intermediate Similarity	NPC58942
0.83	Intermediate Similarity	NPC477928
0.8286	Intermediate Similarity	NPC57362
0.8286	Intermediate Similarity	NPC237503
0.8286	Intermediate Similarity	NPC127853
0.8286	Intermediate Similarity	NPC204407
0.8286	Intermediate Similarity	NPC167383
0.8286	Intermediate Similarity	NPC306746
0.8283	Intermediate Similarity	NPC88847
0.8283	Intermediate Similarity	NPC471903
0.8283	Intermediate Similarity	NPC204961
0.8283	Intermediate Similarity	NPC173744
0.8283	Intermediate Similarity	NPC304899
0.8283	Intermediate Similarity	NPC253115
0.8283	Intermediate Similarity	NPC73004
0.828	Intermediate Similarity	NPC238992
0.8269	Intermediate Similarity	NPC283849
0.8265	Intermediate Similarity	NPC299996
0.8265	Intermediate Similarity	NPC32407
0.8265	Intermediate Similarity	NPC88116
0.8265	Intermediate Similarity	NPC20235
0.8265	Intermediate Similarity	NPC145667
0.8265	Intermediate Similarity	NPC263548
0.8265	Intermediate Similarity	NPC231063
0.8265	Intermediate Similarity	NPC282395
0.8261	Intermediate Similarity	NPC286786
0.8261	Intermediate Similarity	NPC47763
0.8252	Intermediate Similarity	NPC54521
0.8252	Intermediate Similarity	NPC230948
0.8252	Intermediate Similarity	NPC473734
0.8252	Intermediate Similarity	NPC57065
0.8252	Intermediate Similarity	NPC109792
0.8247	Intermediate Similarity	NPC235884
0.8247	Intermediate Similarity	NPC300351
0.8247	Intermediate Similarity	NPC77099
0.8247	Intermediate Similarity	NPC52021
0.8247	Intermediate Similarity	NPC475708
0.8247	Intermediate Similarity	NPC306541
0.8247	Intermediate Similarity	NPC60755
0.8247	Intermediate Similarity	NPC25299
0.8247	Intermediate Similarity	NPC71074
0.8247	Intermediate Similarity	NPC470590
0.8247	Intermediate Similarity	NPC285184
0.8247	Intermediate Similarity	NPC84319
0.8247	Intermediate Similarity	NPC472149
0.8241	Intermediate Similarity	NPC475633
0.8235	Intermediate Similarity	NPC475344
0.8235	Intermediate Similarity	NPC470053
0.8235	Intermediate Similarity	NPC11956
0.8235	Intermediate Similarity	NPC476471
0.8229	Intermediate Similarity	NPC259875
0.8229	Intermediate Similarity	NPC187785
0.8224	Intermediate Similarity	NPC46388
0.8224	Intermediate Similarity	NPC195132
0.8224	Intermediate Similarity	NPC139894
0.8224	Intermediate Similarity	NPC48249
0.8224	Intermediate Similarity	NPC161434
0.8224	Intermediate Similarity	NPC128925
0.8224	Intermediate Similarity	NPC473383
0.8224	Intermediate Similarity	NPC37739
0.8224	Intermediate Similarity	NPC256798
0.8208	Intermediate Similarity	NPC164194
0.8208	Intermediate Similarity	NPC279554
0.8208	Intermediate Similarity	NPC220984
0.8208	Intermediate Similarity	NPC56713
0.8208	Intermediate Similarity	NPC136877
0.8208	Intermediate Similarity	NPC270667
0.8208	Intermediate Similarity	NPC177047
0.8208	Intermediate Similarity	NPC59804
0.8208	Intermediate Similarity	NPC90856
0.8208	Intermediate Similarity	NPC174679
0.8208	Intermediate Similarity	NPC475296
0.8208	Intermediate Similarity	NPC29069
0.8208	Intermediate Similarity	NPC127056
0.8208	Intermediate Similarity	NPC474589
0.82	Intermediate Similarity	NPC247139
0.82	Intermediate Similarity	NPC51499
0.82	Intermediate Similarity	NPC255589
0.82	Intermediate Similarity	NPC9613
0.82	Intermediate Similarity	NPC259788
0.819	Intermediate Similarity	NPC476123
0.819	Intermediate Similarity	NPC284807
0.819	Intermediate Similarity	NPC285576
0.819	Intermediate Similarity	NPC177246
0.819	Intermediate Similarity	NPC28198
0.8182	Intermediate Similarity	NPC195715
0.8182	Intermediate Similarity	NPC96916
0.8182	Intermediate Similarity	NPC32118
0.8173	Intermediate Similarity	NPC138057
0.8172	Intermediate Similarity	NPC253402
0.8172	Intermediate Similarity	NPC159168
0.8163	Intermediate Similarity	NPC275809
0.8163	Intermediate Similarity	NPC133579
0.8163	Intermediate Similarity	NPC474806
0.8155	Intermediate Similarity	NPC23584
0.8152	Intermediate Similarity	NPC108476
0.8152	Intermediate Similarity	NPC290495
0.8152	Intermediate Similarity	NPC195334
0.8152	Intermediate Similarity	NPC242350
0.8148	Intermediate Similarity	NPC96641
0.8148	Intermediate Similarity	NPC73318
0.8148	Intermediate Similarity	NPC150400
0.8148	Intermediate Similarity	NPC204458
0.8148	Intermediate Similarity	NPC189884
0.8148	Intermediate Similarity	NPC124296
0.8148	Intermediate Similarity	NPC163183
0.8148	Intermediate Similarity	NPC475208
0.8148	Intermediate Similarity	NPC473343

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 NPC474571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1609
0.2-0.3	3879
0.3-0.4	2272
0.4-0.5	777
0.5-0.6	263
0.6-0.7	125
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7935	Intermediate Similarity	NPD7645	Phase 2
0.79	Intermediate Similarity	NPD7748	Approved
0.77	Intermediate Similarity	NPD7515	Phase 2
0.767	Intermediate Similarity	NPD7902	Approved
0.7615	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7524	Approved
0.7456	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7638	Approved
0.7379	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7900	Approved
0.7373	Intermediate Similarity	NPD8328	Phase 3
0.7358	Intermediate Similarity	NPD7639	Approved
0.7358	Intermediate Similarity	NPD7640	Approved
0.735	Intermediate Similarity	NPD8033	Approved
0.735	Intermediate Similarity	NPD8296	Approved
0.735	Intermediate Similarity	NPD8380	Approved
0.735	Intermediate Similarity	NPD8378	Approved
0.735	Intermediate Similarity	NPD8379	Approved
0.735	Intermediate Similarity	NPD8335	Approved
0.7328	Intermediate Similarity	NPD7516	Approved
0.7265	Intermediate Similarity	NPD8294	Approved
0.7265	Intermediate Similarity	NPD8377	Approved
0.7241	Intermediate Similarity	NPD7328	Approved
0.7241	Intermediate Similarity	NPD7327	Approved
0.7203	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5344	Discontinued
0.7103	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD6695	Phase 3
0.7037	Intermediate Similarity	NPD6648	Approved
0.7019	Intermediate Similarity	NPD6411	Approved
0.7019	Intermediate Similarity	NPD7637	Suspended
0.7019	Intermediate Similarity	NPD8034	Phase 2
0.7019	Intermediate Similarity	NPD8035	Phase 2
0.7	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD7750	Discontinued
0.6952	Remote Similarity	NPD6399	Phase 3
0.6939	Remote Similarity	NPD7525	Registered
0.6931	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8133	Approved
0.6864	Remote Similarity	NPD7115	Discovery
0.6837	Remote Similarity	NPD6929	Approved
0.6827	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6101	Approved
0.681	Remote Similarity	NPD8297	Approved
0.6792	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6942	Approved
0.6771	Remote Similarity	NPD7339	Approved
0.6768	Remote Similarity	NPD6931	Approved
0.6768	Remote Similarity	NPD6930	Phase 2
0.6762	Remote Similarity	NPD7838	Discovery
0.6757	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD6686	Approved
0.6752	Remote Similarity	NPD4632	Approved
0.6726	Remote Similarity	NPD6402	Approved
0.6726	Remote Similarity	NPD7128	Approved
0.6726	Remote Similarity	NPD5739	Approved
0.6726	Remote Similarity	NPD6675	Approved
0.672	Remote Similarity	NPD7736	Approved
0.6701	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6933	Approved
0.6694	Remote Similarity	NPD6319	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD8517	Approved
0.6634	Remote Similarity	NPD3667	Approved
0.6633	Remote Similarity	NPD6925	Approved
0.6633	Remote Similarity	NPD5776	Phase 2
0.6633	Remote Similarity	NPD6932	Approved
0.6609	Remote Similarity	NPD7320	Approved
0.6609	Remote Similarity	NPD6899	Approved
0.6609	Remote Similarity	NPD6881	Approved
0.6598	Remote Similarity	NPD8264	Approved
0.6581	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7145	Approved
0.6552	Remote Similarity	NPD6373	Approved
0.6552	Remote Similarity	NPD6372	Approved
0.6545	Remote Similarity	NPD6084	Phase 2
0.6545	Remote Similarity	NPD6083	Phase 2
0.6542	Remote Similarity	NPD7087	Discontinued
0.6542	Remote Similarity	NPD7983	Approved
0.6538	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD5697	Approved
0.6522	Remote Similarity	NPD5701	Approved
0.6522	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5328	Approved
0.6508	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD6683	Phase 2
0.6496	Remote Similarity	NPD7102	Approved
0.6496	Remote Similarity	NPD7290	Approved
0.6496	Remote Similarity	NPD6883	Approved
0.6495	Remote Similarity	NPD6926	Approved
0.6495	Remote Similarity	NPD6924	Approved
0.648	Remote Similarity	NPD7492	Approved
0.6449	Remote Similarity	NPD3168	Discontinued
0.6446	Remote Similarity	NPD6009	Approved
0.6442	Remote Similarity	NPD6893	Approved
0.6441	Remote Similarity	NPD6649	Approved
0.6441	Remote Similarity	NPD6869	Approved
0.6441	Remote Similarity	NPD6650	Approved
0.6441	Remote Similarity	NPD6617	Approved
0.6441	Remote Similarity	NPD6847	Approved
0.6436	Remote Similarity	NPD7332	Phase 2
0.6436	Remote Similarity	NPD7514	Phase 3
0.6435	Remote Similarity	NPD6008	Approved
0.6429	Remote Similarity	NPD6616	Approved
0.6423	Remote Similarity	NPD6054	Approved
0.6423	Remote Similarity	NPD6059	Approved
0.641	Remote Similarity	NPD6012	Approved
0.641	Remote Similarity	NPD6013	Approved
0.641	Remote Similarity	NPD6014	Approved
0.64	Remote Similarity	NPD7604	Phase 2
0.6389	Remote Similarity	NPD6079	Approved
0.6387	Remote Similarity	NPD6882	Approved
0.6381	Remote Similarity	NPD7146	Approved
0.6381	Remote Similarity	NPD6684	Approved
0.6381	Remote Similarity	NPD7521	Approved
0.6381	Remote Similarity	NPD6409	Approved
0.6381	Remote Similarity	NPD7334	Approved
0.6381	Remote Similarity	NPD5330	Approved
0.6378	Remote Similarity	NPD7078	Approved
0.6373	Remote Similarity	NPD6902	Approved
0.6373	Remote Similarity	NPD6898	Phase 1
0.6372	Remote Similarity	NPD4159	Approved
0.6371	Remote Similarity	NPD5983	Phase 2
0.6355	Remote Similarity	NPD6051	Approved
0.6325	Remote Similarity	NPD6011	Approved
0.6321	Remote Similarity	NPD3573	Approved
0.6321	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6370	Approved
0.6303	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6336	Discontinued
0.6296	Remote Similarity	NPD46	Approved
0.6296	Remote Similarity	NPD6698	Approved
0.6289	Remote Similarity	NPD7150	Approved
0.6289	Remote Similarity	NPD7152	Approved
0.6289	Remote Similarity	NPD7151	Approved
0.6275	Remote Similarity	NPD7509	Discontinued
0.6262	Remote Similarity	NPD6672	Approved
0.6262	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD6922	Approved
0.625	Remote Similarity	NPD4755	Approved
0.624	Remote Similarity	NPD6016	Approved
0.624	Remote Similarity	NPD6015	Approved
0.624	Remote Similarity	NPD6921	Approved
0.6238	Remote Similarity	NPD6118	Approved
0.6238	Remote Similarity	NPD6697	Approved
0.6238	Remote Similarity	NPD6115	Approved
0.6238	Remote Similarity	NPD6114	Approved
0.6218	Remote Similarity	NPD4634	Approved
0.6216	Remote Similarity	NPD5695	Phase 3
0.6195	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD3668	Phase 3
0.619	Remote Similarity	NPD3665	Phase 1
0.619	Remote Similarity	NPD3133	Approved
0.619	Remote Similarity	NPD5988	Approved
0.619	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD7144	Approved
0.6186	Remote Similarity	NPD7143	Approved
0.6182	Remote Similarity	NPD4202	Approved
0.6182	Remote Similarity	NPD8171	Discontinued
0.6174	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5221	Approved
0.6161	Remote Similarity	NPD5222	Approved
0.6161	Remote Similarity	NPD4697	Phase 3
0.6161	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6640	Phase 3
0.6142	Remote Similarity	NPD6067	Discontinued
0.614	Remote Similarity	NPD4700	Approved
0.614	Remote Similarity	NPD5286	Approved
0.614	Remote Similarity	NPD5285	Approved
0.614	Remote Similarity	NPD4696	Approved
0.6124	Remote Similarity	NPD8074	Phase 3
0.6117	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5173	Approved
0.6098	Remote Similarity	NPD6868	Approved
0.6098	Remote Similarity	NPD6274	Approved
0.6082	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7101	Approved
0.608	Remote Similarity	NPD7100	Approved
0.6075	Remote Similarity	NPD5279	Phase 3
0.6071	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4753	Phase 2
0.604	Remote Similarity	NPD6117	Approved
0.6038	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5224	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