NPASS Compound

Structure

NPC96784 OpenBabel07101718252D 37 41 0 0 1 0 0 0 0 0999 V2000 5.0724 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5124 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0243 0.6189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3816 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3816 3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5362 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 2.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 2.4405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 2.4405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 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 -0.8454 1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2270 4.3929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 2.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 19 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 12 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 29 1 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 2 1 1 0 0 0 18 23 1 0 0 0 0 19 33 2 0 0 0 0 19 37 1 0 0 0 0 20 23 1 0 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 34 1 6 0 0 0 22 28 1 0 0 0 0 22 32 1 1 0 0 0 23 29 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 6 0 0 0 25 31 1 1 0 0 0 25 32 1 0 0 0 0 26 32 1 1 0 0 0 26 36 1 0 0 0 0 27 28 1 0 0 0 0 27 37 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:	516.38
Volume:	557.924
LogP:	5.667
LogD:	4.829
LogS:	-4.823
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	5.373
Fsp3:	0.906
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.891
MDCK Permeability:	1.806194086384494e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.466
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	92.15565490722656%
Volume Distribution (VD):	1.58
Pgp-substrate:	3.1455934047698975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.578
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	3.21
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.308
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.629
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.06
Carcinogencity:	0.027
Eye Corrosion:	0.004
Eye Irritation:	0.009
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC96784

Natural Product ID:	NPC96784
*Common Name:**	3Beta-Acetoxyurs-12-Ene-1Beta,2Alpha,11Alpha-Triol
IUPAC Name:	[(1S,2R,3R,4aS,6aR,6bS,8aR,11R,12S,12aR,14R,14aS,14bS)-1,2,14-trihydroxy-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] acetate
Synonyms:
Standard InCHIKey:	RMIQORJYWWJQBI-XWVSFCHWSA-N
Standard InCHI:	InChI=1S/C32H52O5/c1-17-10-12-29(6)14-15-30(7)20(23(29)18(17)2)16-21(34)25-31(30,8)13-11-22-28(4,5)27(37-19(3)33)24(35)26(36)32(22,25)9/h16-18,21-27,34-36H,10-15H2,1-9H3/t17-,18+,21-,22+,23+,24-,25+,26-,27+,29-,30-,31-,32+/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2[C@H](O)C=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@H](C)CC1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514350
PubChem CID:	22212738
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	=	32.5	ug.mL-1	PMID[529368]

☑ 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 NPC96784 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	234
0.1-0.2	1593
0.2-0.3	4691
0.3-0.4	9877
0.4-0.5	12698
0.5-0.6	5971
0.6-0.7	4653
0.7-0.8	2441
0.8-0.85	474
0.85-0.9	51
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235920
0.9574	High Similarity	NPC477876
0.9574	High Similarity	NPC477875
0.9368	High Similarity	NPC247233
0.9271	High Similarity	NPC254567
0.9271	High Similarity	NPC474571
0.9175	High Similarity	NPC476132
0.91	High Similarity	NPC473586
0.9072	High Similarity	NPC476195
0.901	High Similarity	NPC475263
0.9	High Similarity	NPC88349
0.9	High Similarity	NPC477877
0.8925	High Similarity	NPC259875
0.8925	High Similarity	NPC187785
0.8889	High Similarity	NPC283343
0.8889	High Similarity	NPC258547
0.8878	High Similarity	NPC474190
0.8788	High Similarity	NPC473160
0.875	High Similarity	NPC215700
0.8713	High Similarity	NPC173583
0.87	High Similarity	NPC273668
0.8673	High Similarity	NPC476878
0.8673	High Similarity	NPC476879
0.8614	High Similarity	NPC162354
0.8614	High Similarity	NPC474124
0.8614	High Similarity	NPC473523
0.8602	High Similarity	NPC137306
0.8602	High Similarity	NPC84121
0.86	High Similarity	NPC475617
0.86	High Similarity	NPC155974
0.8586	High Similarity	NPC102426
0.8586	High Similarity	NPC325229
0.8586	High Similarity	NPC300179
0.8586	High Similarity	NPC275086
0.8571	High Similarity	NPC230151
0.8571	High Similarity	NPC19376
0.8571	High Similarity	NPC25848
0.8571	High Similarity	NPC307282
0.8571	High Similarity	NPC305464
0.8558	High Similarity	NPC310546
0.8542	High Similarity	NPC41239
0.8529	High Similarity	NPC470768
0.8529	High Similarity	NPC473543
0.8519	High Similarity	NPC471547
0.8515	High Similarity	NPC475344
0.8515	High Similarity	NPC476471
0.85	High Similarity	NPC208358
0.85	High Similarity	NPC473790
0.8495	Intermediate Similarity	NPC191965
0.8485	Intermediate Similarity	NPC51499
0.8476	Intermediate Similarity	NPC476886
0.8476	Intermediate Similarity	NPC476881
0.8476	Intermediate Similarity	NPC7870
0.8476	Intermediate Similarity	NPC476880
0.8476	Intermediate Similarity	NPC476887
0.8476	Intermediate Similarity	NPC110139
0.8476	Intermediate Similarity	NPC476883
0.8476	Intermediate Similarity	NPC476882
0.8476	Intermediate Similarity	NPC75747
0.8476	Intermediate Similarity	NPC102914
0.8476	Intermediate Similarity	NPC199457
0.8476	Intermediate Similarity	NPC476885
0.8476	Intermediate Similarity	NPC476884
0.8476	Intermediate Similarity	NPC108709
0.8476	Intermediate Similarity	NPC68419
0.8469	Intermediate Similarity	NPC474727
0.8431	Intermediate Similarity	NPC473123
0.8431	Intermediate Similarity	NPC473124
0.8416	Intermediate Similarity	NPC233012
0.8416	Intermediate Similarity	NPC256247
0.8416	Intermediate Similarity	NPC54909
0.8416	Intermediate Similarity	NPC289670
0.8404	Intermediate Similarity	NPC237344
0.84	Intermediate Similarity	NPC470068
0.8396	Intermediate Similarity	NPC179434
0.8387	Intermediate Similarity	NPC102048
0.8384	Intermediate Similarity	NPC471765
0.8384	Intermediate Similarity	NPC221801
0.8384	Intermediate Similarity	NPC169270
0.8384	Intermediate Similarity	NPC292718
0.8384	Intermediate Similarity	NPC88009
0.8384	Intermediate Similarity	NPC306797
0.8384	Intermediate Similarity	NPC211810
0.8384	Intermediate Similarity	NPC111834
0.8384	Intermediate Similarity	NPC284194
0.8381	Intermediate Similarity	NPC167383
0.8381	Intermediate Similarity	NPC204407
0.8381	Intermediate Similarity	NPC127853
0.8381	Intermediate Similarity	NPC57362
0.8381	Intermediate Similarity	NPC306746
0.8381	Intermediate Similarity	NPC237503
0.8367	Intermediate Similarity	NPC20235
0.8367	Intermediate Similarity	NPC296164
0.8367	Intermediate Similarity	NPC263548
0.8367	Intermediate Similarity	NPC88116
0.8367	Intermediate Similarity	NPC231063
0.8367	Intermediate Similarity	NPC145667
0.8367	Intermediate Similarity	NPC299996
0.8367	Intermediate Similarity	NPC32407
0.8367	Intermediate Similarity	NPC282395
0.8365	Intermediate Similarity	NPC283849
0.8365	Intermediate Similarity	NPC471205
0.835	Intermediate Similarity	NPC152966
0.835	Intermediate Similarity	NPC203354
0.835	Intermediate Similarity	NPC110656
0.835	Intermediate Similarity	NPC473127
0.8349	Intermediate Similarity	NPC473405
0.8333	Intermediate Similarity	NPC16265
0.8333	Intermediate Similarity	NPC110861
0.8333	Intermediate Similarity	NPC246028
0.8318	Intermediate Similarity	NPC473383
0.8318	Intermediate Similarity	NPC473125
0.8318	Intermediate Similarity	NPC48249
0.8318	Intermediate Similarity	NPC139894
0.8318	Intermediate Similarity	NPC116794
0.8317	Intermediate Similarity	NPC473510
0.8317	Intermediate Similarity	NPC230546
0.8317	Intermediate Similarity	NPC38855
0.8302	Intermediate Similarity	NPC270667
0.8302	Intermediate Similarity	NPC59804
0.8302	Intermediate Similarity	NPC164194
0.8302	Intermediate Similarity	NPC90856
0.8302	Intermediate Similarity	NPC220984
0.8302	Intermediate Similarity	NPC174679
0.8302	Intermediate Similarity	NPC29069
0.8302	Intermediate Similarity	NPC127056
0.8302	Intermediate Similarity	NPC474589
0.8302	Intermediate Similarity	NPC279554
0.8302	Intermediate Similarity	NPC274507
0.8302	Intermediate Similarity	NPC475296
0.8302	Intermediate Similarity	NPC136877
0.8302	Intermediate Similarity	NPC56713
0.83	Intermediate Similarity	NPC473244
0.83	Intermediate Similarity	NPC475032
0.83	Intermediate Similarity	NPC43686
0.83	Intermediate Similarity	NPC475033
0.83	Intermediate Similarity	NPC210337
0.8286	Intermediate Similarity	NPC472219
0.8286	Intermediate Similarity	NPC88701
0.8286	Intermediate Similarity	NPC476123
0.8286	Intermediate Similarity	NPC284807
0.8286	Intermediate Similarity	NPC472218
0.8286	Intermediate Similarity	NPC177246
0.8286	Intermediate Similarity	NPC472217
0.8286	Intermediate Similarity	NPC28198
0.8283	Intermediate Similarity	NPC241047
0.828	Intermediate Similarity	NPC159168
0.828	Intermediate Similarity	NPC253402
0.8273	Intermediate Similarity	NPC471548
0.8273	Intermediate Similarity	NPC470515
0.8269	Intermediate Similarity	NPC470763
0.8269	Intermediate Similarity	NPC470767
0.8269	Intermediate Similarity	NPC80566
0.8265	Intermediate Similarity	NPC74855
0.8265	Intermediate Similarity	NPC119379
0.8265	Intermediate Similarity	NPC136313
0.8265	Intermediate Similarity	NPC86368
0.8265	Intermediate Similarity	NPC307335
0.8257	Intermediate Similarity	NPC268954
0.8252	Intermediate Similarity	NPC281378
0.8241	Intermediate Similarity	NPC49413
0.8241	Intermediate Similarity	NPC134835
0.8241	Intermediate Similarity	NPC73318
0.8241	Intermediate Similarity	NPC44298
0.8241	Intermediate Similarity	NPC40133
0.8241	Intermediate Similarity	NPC473343
0.8241	Intermediate Similarity	NPC473128
0.8241	Intermediate Similarity	NPC475208
0.8241	Intermediate Similarity	NPC290608
0.8241	Intermediate Similarity	NPC96641
0.8241	Intermediate Similarity	NPC238935
0.8241	Intermediate Similarity	NPC271138
0.8241	Intermediate Similarity	NPC150400
0.8241	Intermediate Similarity	NPC269315
0.8241	Intermediate Similarity	NPC473159
0.8241	Intermediate Similarity	NPC163183
0.8235	Intermediate Similarity	NPC472554
0.8235	Intermediate Similarity	NPC263756
0.8235	Intermediate Similarity	NPC117714
0.8235	Intermediate Similarity	NPC470054
0.8224	Intermediate Similarity	NPC235841
0.8224	Intermediate Similarity	NPC191763
0.8224	Intermediate Similarity	NPC473481
0.8224	Intermediate Similarity	NPC164419
0.8224	Intermediate Similarity	NPC31839
0.8224	Intermediate Similarity	NPC297208
0.8224	Intermediate Similarity	NPC108748
0.8224	Intermediate Similarity	NPC30397
0.8224	Intermediate Similarity	NPC211798
0.8218	Intermediate Similarity	NPC260149
0.8218	Intermediate Similarity	NPC470067
0.8218	Intermediate Similarity	NPC470066
0.8218	Intermediate Similarity	NPC477928
0.8218	Intermediate Similarity	NPC58942
0.8208	Intermediate Similarity	NPC125361
0.8208	Intermediate Similarity	NPC472534
0.8208	Intermediate Similarity	NPC154085
0.8208	Intermediate Similarity	NPC51925
0.8208	Intermediate Similarity	NPC137917
0.8208	Intermediate Similarity	NPC296761

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 NPC96784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1823
0.2-0.3	3888
0.3-0.4	2127
0.4-0.5	704
0.5-0.6	266
0.6-0.7	112
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7849	Intermediate Similarity	NPD7645	Phase 2
0.7822	Intermediate Similarity	NPD7748	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7788	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7902	Approved
0.7739	Intermediate Similarity	NPD8335	Approved
0.7739	Intermediate Similarity	NPD8379	Approved
0.7739	Intermediate Similarity	NPD8378	Approved
0.7739	Intermediate Similarity	NPD8296	Approved
0.7739	Intermediate Similarity	NPD8380	Approved
0.7719	Intermediate Similarity	NPD7516	Approved
0.7706	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7638	Approved
0.7652	Intermediate Similarity	NPD8294	Approved
0.7652	Intermediate Similarity	NPD8377	Approved
0.7632	Intermediate Similarity	NPD7328	Approved
0.7632	Intermediate Similarity	NPD7327	Approved
0.7624	Intermediate Similarity	NPD7515	Phase 2
0.7586	Intermediate Similarity	NPD8033	Approved
0.7547	Intermediate Similarity	NPD5344	Discontinued
0.7545	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7900	Approved
0.7476	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8328	Phase 3
0.7391	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4225	Approved
0.7288	Intermediate Similarity	NPD7503	Approved
0.7228	Intermediate Similarity	NPD7524	Approved
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6648	Approved
0.713	Intermediate Similarity	NPD8133	Approved
0.7115	Intermediate Similarity	NPD8035	Phase 2
0.7115	Intermediate Similarity	NPD8034	Phase 2
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7049	Intermediate Similarity	NPD7507	Approved
0.7041	Intermediate Similarity	NPD7525	Registered
0.7016	Intermediate Similarity	NPD7319	Approved
0.6952	Remote Similarity	NPD7637	Suspended
0.6931	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8297	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.6863	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4632	Approved
0.6832	Remote Similarity	NPD6695	Phase 3
0.6814	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6777	Remote Similarity	NPD6319	Approved
0.6731	Remote Similarity	NPD7750	Discontinued
0.6729	Remote Similarity	NPD5778	Approved
0.6729	Remote Similarity	NPD5779	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6698	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6638	Remote Similarity	NPD6372	Approved
0.6638	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.6609	Remote Similarity	NPD5701	Approved
0.6609	Remote Similarity	NPD5697	Approved
0.6604	Remote Similarity	NPD6051	Approved
0.66	Remote Similarity	NPD6929	Approved
0.6587	Remote Similarity	NPD8293	Discontinued
0.6581	Remote Similarity	NPD7290	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7492	Approved
0.6542	Remote Similarity	NPD46	Approved
0.6542	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD6931	Approved
0.6535	Remote Similarity	NPD6930	Phase 2
0.6531	Remote Similarity	NPD6942	Approved
0.6531	Remote Similarity	NPD8264	Approved
0.6531	Remote Similarity	NPD7339	Approved
0.6529	Remote Similarity	NPD6009	Approved
0.6525	Remote Similarity	NPD6649	Approved
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD6650	Approved
0.6525	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6616	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.6504	Remote Similarity	NPD6054	Approved
0.6496	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6084	Phase 2
0.6486	Remote Similarity	NPD6083	Phase 2
0.6481	Remote Similarity	NPD6411	Approved
0.648	Remote Similarity	NPD7604	Phase 2
0.6476	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD6882	Approved
0.6465	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4159	Approved
0.6457	Remote Similarity	NPD7078	Approved
0.6452	Remote Similarity	NPD6921	Approved
0.6452	Remote Similarity	NPD5983	Phase 2
0.6449	Remote Similarity	NPD5328	Approved
0.6442	Remote Similarity	NPD4786	Approved
0.641	Remote Similarity	NPD6011	Approved
0.6408	Remote Similarity	NPD3667	Approved
0.6404	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD6370	Approved
0.64	Remote Similarity	NPD5776	Phase 2
0.64	Remote Similarity	NPD6925	Approved
0.6389	Remote Similarity	NPD3168	Discontinued
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6008	Approved
0.6378	Remote Similarity	NPD6336	Discontinued
0.6373	Remote Similarity	NPD7332	Phase 2
0.6373	Remote Similarity	NPD7514	Phase 3
0.6339	Remote Similarity	NPD4755	Approved
0.6337	Remote Similarity	NPD7145	Approved
0.633	Remote Similarity	NPD6079	Approved
0.633	Remote Similarity	NPD7087	Discontinued
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.632	Remote Similarity	NPD6016	Approved
0.632	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD6902	Approved
0.6303	Remote Similarity	NPD4634	Approved
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6293	Remote Similarity	NPD5141	Approved
0.6286	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8171	Discontinued
0.6273	Remote Similarity	NPD4202	Approved
0.627	Remote Similarity	NPD5988	Approved
0.6262	Remote Similarity	NPD3573	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD4700	Approved
0.6226	Remote Similarity	NPD6893	Approved
0.622	Remote Similarity	NPD6067	Discontinued
0.6214	Remote Similarity	NPD7625	Phase 1
0.6204	Remote Similarity	NPD6672	Approved
0.6204	Remote Similarity	NPD6903	Approved
0.6204	Remote Similarity	NPD5737	Approved
0.6202	Remote Similarity	NPD8074	Phase 3
0.6198	Remote Similarity	NPD6053	Discontinued
0.6179	Remote Similarity	NPD6274	Approved
0.6176	Remote Similarity	NPD6118	Approved
0.6176	Remote Similarity	NPD6114	Approved
0.6176	Remote Similarity	NPD6697	Approved
0.6176	Remote Similarity	NPD6115	Approved
0.6167	Remote Similarity	NPD6371	Approved
0.6161	Remote Similarity	NPD5695	Phase 3
0.616	Remote Similarity	NPD7101	Approved
0.616	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD6898	Phase 1
0.614	Remote Similarity	NPD5696	Approved
0.6139	Remote Similarity	NPD6933	Approved
0.6132	Remote Similarity	NPD3666	Approved
0.6132	Remote Similarity	NPD3665	Phase 1
0.6132	Remote Similarity	NPD3133	Approved
0.6122	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.6106	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5222	Approved
0.6106	Remote Similarity	NPD5221	Approved
0.6106	Remote Similarity	NPD4697	Phase 3
0.6102	Remote Similarity	NPD6640	Phase 3
0.6095	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6335	Approved
0.6078	Remote Similarity	NPD6932	Approved
0.6078	Remote Similarity	NPD6116	Phase 1
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD6909	Approved
0.6063	Remote Similarity	NPD6908	Approved
0.6058	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5173	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