NPASS Compound

Structure

NPC177047 OpenBabel07101718192D 34 37 0 0 1 0 0 0 0 0999 V2000 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7812 0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 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 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 13 26 2 0 0 0 0 13 32 1 0 0 0 0 14 27 2 0 0 0 0 14 33 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 1 0 0 0 17 23 1 6 0 0 0 17 32 1 0 0 0 0 18 28 2 0 0 0 0 18 34 1 0 0 0 0 19 12 1 6 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 25 1 6 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 23 25 1 1 0 0 0 24 31 1 6 0 0 0 24 34 1 0 0 0 0 25 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.22
Volume:	472.66
LogP:	1.771
LogD:	1.389
LogS:	-3.633
# Rotatable Bonds:	5
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	5.387
Fsp3:	0.72
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:	-5.091
MDCK Permeability:	6.480895535787567e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.25
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.661
Plasma Protein Binding (PPB):	48.9070930480957%
Volume Distribution (VD):	1.264
Pgp-substrate:	49.436031341552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	2.625
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.41
Human Hepatotoxicity (H-HT):	0.548
Drug-inuced Liver Injury (DILI):	0.429
AMES Toxicity:	0.854
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.196
Skin Sensitization:	0.485
Carcinogencity:	0.673
Eye Corrosion:	0.007
Eye Irritation:	0.011
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC177047

Natural Product ID:	NPC177047
*Common Name:**	1Alpha,6Alpha-Diacetoxy-5Alpha,7Beta-Dihydroxy-12Alpha-Methoxycassa-14(17),13(15)-Dien-16,12-Olide
IUPAC Name:	[(1S,4aR,5S,6R,6aR,10aR,11aS,11bS)-5-acetyloxy-4a,6-dihydroxy-10a-methoxy-4,4,11b-trimethyl-7-methylidene-9-oxo-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	FZORVJMAWWTYLA-JLHWGCSWSA-N
Standard InCHI:	InChI=1S/C25H34O9/c1-12-15-10-18(28)34-24(15,31-7)11-16-19(12)20(29)21(33-14(3)27)25(30)22(4,5)9-8-17(23(16,25)6)32-13(2)26/h10,16-17,19-21,29-30H,1,8-9,11H2,2-7H3/t16-,17-,19-,20+,21-,23-,24+,25+/m0/s1
SMILES:	CO[C@@]12OC(=O)C=C2C(=C)[C@H]2[C@H](C1)[C@@]1(C)[C@H](CCC([C@@]1([C@H]([C@@H]2O)OC(=O)C)O)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386708
PubChem CID:	71725698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678648]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[23806110]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24303808]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14392	Caesalpinia minax	Species	Fabaceae	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
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[482726]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	38900.0	nM	PMID[482726]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[482726]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[482726]

☑ 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 NPC177047 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	1373
0.2-0.3	4056
0.3-0.4	6756
0.4-0.5	13196
0.5-0.6	8642
0.6-0.7	5519
0.7-0.8	2595
0.8-0.85	297
0.85-0.9	28
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC51719
0.9406	High Similarity	NPC45897
0.9406	High Similarity	NPC281378
0.932	High Similarity	NPC471205
0.932	High Similarity	NPC122816
0.9048	High Similarity	NPC50124
0.902	High Similarity	NPC472554
0.8962	High Similarity	NPC206618
0.8932	High Similarity	NPC472552
0.8932	High Similarity	NPC11956
0.8922	High Similarity	NPC38855
0.8868	High Similarity	NPC38948
0.8857	High Similarity	NPC471206
0.8846	High Similarity	NPC23584
0.8835	High Similarity	NPC11974
0.875	High Similarity	NPC268326
0.875	High Similarity	NPC153085
0.8739	High Similarity	NPC34390
0.8739	High Similarity	NPC196429
0.8739	High Similarity	NPC77319
0.8739	High Similarity	NPC158344
0.8739	High Similarity	NPC471351
0.8739	High Similarity	NPC471353
0.8739	High Similarity	NPC87250
0.8739	High Similarity	NPC309034
0.8739	High Similarity	NPC471354
0.8739	High Similarity	NPC244402
0.8739	High Similarity	NPC471355
0.8739	High Similarity	NPC152615
0.8739	High Similarity	NPC157376
0.8739	High Similarity	NPC84987
0.8739	High Similarity	NPC99728
0.8739	High Similarity	NPC50305
0.8739	High Similarity	NPC474418
0.8739	High Similarity	NPC473852
0.8739	High Similarity	NPC243196
0.8739	High Similarity	NPC142066
0.8739	High Similarity	NPC27507
0.8716	High Similarity	NPC317460
0.8716	High Similarity	NPC328074
0.8716	High Similarity	NPC470025
0.8716	High Similarity	NPC321272
0.8713	High Similarity	NPC276110
0.8704	High Similarity	NPC316708
0.8692	High Similarity	NPC181994
0.8673	High Similarity	NPC475136
0.8673	High Similarity	NPC474466
0.8667	High Similarity	NPC120009
0.8661	High Similarity	NPC83287
0.8649	High Similarity	NPC199428
0.8649	High Similarity	NPC99620
0.8649	High Similarity	NPC5311
0.8649	High Similarity	NPC193382
0.8649	High Similarity	NPC310341
0.8641	High Similarity	NPC278673
0.8636	High Similarity	NPC470027
0.8624	High Similarity	NPC470026
0.8624	High Similarity	NPC17791
0.8611	High Similarity	NPC316974
0.8598	High Similarity	NPC475074
0.8598	High Similarity	NPC473586
0.8584	High Similarity	NPC329905
0.8584	High Similarity	NPC304260
0.8584	High Similarity	NPC5883
0.8584	High Similarity	NPC44899
0.8584	High Similarity	NPC29639
0.8571	High Similarity	NPC203862
0.8571	High Similarity	NPC121423
0.8571	High Similarity	NPC93883
0.8559	High Similarity	NPC69576
0.8559	High Similarity	NPC471633
0.8559	High Similarity	NPC31354
0.8559	High Similarity	NPC84949
0.8544	High Similarity	NPC51499
0.8519	High Similarity	NPC128795
0.8519	High Similarity	NPC135015
0.8519	High Similarity	NPC48548
0.8519	High Similarity	NPC217921
0.8519	High Similarity	NPC311223
0.8519	High Similarity	NPC475263
0.8509	High Similarity	NPC475629
0.8509	High Similarity	NPC475556
0.8505	High Similarity	NPC82251
0.8505	High Similarity	NPC218158
0.8491	Intermediate Similarity	NPC474124
0.8491	Intermediate Similarity	NPC474822
0.8491	Intermediate Similarity	NPC474575
0.8482	Intermediate Similarity	NPC471816
0.8476	Intermediate Similarity	NPC475617
0.8462	Intermediate Similarity	NPC275086
0.8462	Intermediate Similarity	NPC325229
0.844	Intermediate Similarity	NPC475030
0.844	Intermediate Similarity	NPC40728
0.8435	Intermediate Similarity	NPC231518
0.8435	Intermediate Similarity	NPC314535
0.8435	Intermediate Similarity	NPC475219
0.8435	Intermediate Similarity	NPC173555
0.8435	Intermediate Similarity	NPC233500
0.8431	Intermediate Similarity	NPC105490
0.8426	Intermediate Similarity	NPC125423
0.8426	Intermediate Similarity	NPC187435
0.8426	Intermediate Similarity	NPC67321
0.8426	Intermediate Similarity	NPC88013
0.8426	Intermediate Similarity	NPC109376
0.8421	Intermediate Similarity	NPC292467
0.8421	Intermediate Similarity	NPC55532
0.8421	Intermediate Similarity	NPC30483
0.8421	Intermediate Similarity	NPC470914
0.8421	Intermediate Similarity	NPC32177
0.8421	Intermediate Similarity	NPC236973
0.8421	Intermediate Similarity	NPC469756
0.8421	Intermediate Similarity	NPC470897
0.8411	Intermediate Similarity	NPC473543
0.8407	Intermediate Similarity	NPC290693
0.8396	Intermediate Similarity	NPC476471
0.8396	Intermediate Similarity	NPC475344
0.8396	Intermediate Similarity	NPC472815
0.8396	Intermediate Similarity	NPC470571
0.8381	Intermediate Similarity	NPC324841
0.8364	Intermediate Similarity	NPC119550
0.8362	Intermediate Similarity	NPC196130
0.8362	Intermediate Similarity	NPC471082
0.8362	Intermediate Similarity	NPC115349
0.8362	Intermediate Similarity	NPC193893
0.8362	Intermediate Similarity	NPC264336
0.8349	Intermediate Similarity	NPC88701
0.8349	Intermediate Similarity	NPC224660
0.8349	Intermediate Similarity	NPC470024
0.8348	Intermediate Similarity	NPC72260
0.8333	Intermediate Similarity	NPC172867
0.8333	Intermediate Similarity	NPC119855
0.8333	Intermediate Similarity	NPC239961
0.8333	Intermediate Similarity	NPC473828
0.8333	Intermediate Similarity	NPC110022
0.8333	Intermediate Similarity	NPC220217
0.8333	Intermediate Similarity	NPC218093
0.8333	Intermediate Similarity	NPC473617
0.8333	Intermediate Similarity	NPC186668
0.8333	Intermediate Similarity	NPC53555
0.8333	Intermediate Similarity	NPC88349
0.8333	Intermediate Similarity	NPC7349
0.8319	Intermediate Similarity	NPC207637
0.8318	Intermediate Similarity	NPC473523
0.8318	Intermediate Similarity	NPC187302
0.8318	Intermediate Similarity	NPC189588
0.8318	Intermediate Similarity	NPC97487
0.8318	Intermediate Similarity	NPC10232
0.8318	Intermediate Similarity	NPC472821
0.8318	Intermediate Similarity	NPC165608
0.8318	Intermediate Similarity	NPC196471
0.8304	Intermediate Similarity	NPC264153
0.8302	Intermediate Similarity	NPC477717
0.8302	Intermediate Similarity	NPC198992
0.8291	Intermediate Similarity	NPC308262
0.8291	Intermediate Similarity	NPC208193
0.8291	Intermediate Similarity	NPC117445
0.8276	Intermediate Similarity	NPC120390
0.8276	Intermediate Similarity	NPC475590
0.8276	Intermediate Similarity	NPC475419
0.8276	Intermediate Similarity	NPC474908
0.8276	Intermediate Similarity	NPC40749
0.8269	Intermediate Similarity	NPC165632
0.8261	Intermediate Similarity	NPC219656
0.8261	Intermediate Similarity	NPC291820
0.8261	Intermediate Similarity	NPC81222
0.8257	Intermediate Similarity	NPC472820
0.8257	Intermediate Similarity	NPC472390
0.8246	Intermediate Similarity	NPC473968
0.8246	Intermediate Similarity	NPC474483
0.8241	Intermediate Similarity	NPC264867
0.8241	Intermediate Similarity	NPC471937
0.8241	Intermediate Similarity	NPC473207
0.8241	Intermediate Similarity	NPC81567
0.8241	Intermediate Similarity	NPC201880
0.8241	Intermediate Similarity	NPC470321
0.8235	Intermediate Similarity	NPC329842
0.8224	Intermediate Similarity	NPC475038
0.8224	Intermediate Similarity	NPC109195
0.8224	Intermediate Similarity	NPC476081
0.8224	Intermediate Similarity	NPC470053
0.8214	Intermediate Similarity	NPC470063
0.8214	Intermediate Similarity	NPC473125
0.8208	Intermediate Similarity	NPC474190
0.8208	Intermediate Similarity	NPC477972
0.8208	Intermediate Similarity	NPC473510
0.8208	Intermediate Similarity	NPC161527
0.8208	Intermediate Similarity	NPC219285
0.8208	Intermediate Similarity	NPC230546
0.8208	Intermediate Similarity	NPC254567
0.8208	Intermediate Similarity	NPC477971
0.8208	Intermediate Similarity	NPC477716
0.8208	Intermediate Similarity	NPC16601
0.8208	Intermediate Similarity	NPC474571
0.8208	Intermediate Similarity	NPC477968
0.8208	Intermediate Similarity	NPC228251
0.8208	Intermediate Similarity	NPC477721
0.8208	Intermediate Similarity	NPC188968
0.8208	Intermediate Similarity	NPC20113
0.8205	Intermediate Similarity	NPC74259
0.8205	Intermediate Similarity	NPC474423

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 NPC177047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1485
0.2-0.3	3665
0.3-0.4	2384
0.4-0.5	949
0.5-0.6	305
0.6-0.7	138
0.7-0.8	20
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7516	Approved
0.8661	High Similarity	NPD7328	Approved
0.8661	High Similarity	NPD7327	Approved
0.8435	Intermediate Similarity	NPD8296	Approved
0.8435	Intermediate Similarity	NPD8335	Approved
0.8435	Intermediate Similarity	NPD8378	Approved
0.8435	Intermediate Similarity	NPD8379	Approved
0.8435	Intermediate Similarity	NPD8033	Approved
0.8435	Intermediate Similarity	NPD8380	Approved
0.8348	Intermediate Similarity	NPD8294	Approved
0.8348	Intermediate Similarity	NPD8377	Approved
0.8182	Intermediate Similarity	NPD6686	Approved
0.812	Intermediate Similarity	NPD7503	Approved
0.8	Intermediate Similarity	NPD7507	Approved
0.7951	Intermediate Similarity	NPD7319	Approved
0.7946	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7638	Approved
0.787	Intermediate Similarity	NPD7639	Approved
0.787	Intermediate Similarity	NPD7640	Approved
0.7798	Intermediate Similarity	NPD5344	Discontinued
0.7719	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6648	Approved
0.7615	Intermediate Similarity	NPD4225	Approved
0.7456	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD8133	Approved
0.7333	Intermediate Similarity	NPD7524	Approved
0.7297	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7838	Discovery
0.7257	Intermediate Similarity	NPD7632	Discontinued
0.719	Intermediate Similarity	NPD7115	Discovery
0.7179	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6412	Phase 2
0.712	Intermediate Similarity	NPD8328	Phase 3
0.7097	Intermediate Similarity	NPD8515	Approved
0.7097	Intermediate Similarity	NPD8513	Phase 3
0.7097	Intermediate Similarity	NPD8516	Approved
0.7097	Intermediate Similarity	NPD8517	Approved
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6882	Approved
0.6972	Remote Similarity	NPD46	Approved
0.6972	Remote Similarity	NPD6698	Approved
0.6952	Remote Similarity	NPD6695	Phase 3
0.6929	Remote Similarity	NPD7492	Approved
0.6911	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6009	Approved
0.6909	Remote Similarity	NPD7637	Suspended
0.6906	Remote Similarity	NPD7625	Phase 1
0.6899	Remote Similarity	NPD7736	Approved
0.6887	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6319	Approved
0.688	Remote Similarity	NPD6054	Approved
0.688	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD6616	Approved
0.686	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD7525	Registered
0.6822	Remote Similarity	NPD8293	Discontinued
0.6822	Remote Similarity	NPD7078	Approved
0.6822	Remote Similarity	NPD8074	Phase 3
0.6803	Remote Similarity	NPD4632	Approved
0.6786	Remote Similarity	NPD7748	Approved
0.678	Remote Similarity	NPD6402	Approved
0.678	Remote Similarity	NPD5739	Approved
0.678	Remote Similarity	NPD7128	Approved
0.678	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6370	Approved
0.6757	Remote Similarity	NPD7515	Phase 2
0.6754	Remote Similarity	NPD7902	Approved
0.675	Remote Similarity	NPD6373	Approved
0.675	Remote Similarity	NPD6372	Approved
0.6697	Remote Similarity	NPD7750	Discontinued
0.6693	Remote Similarity	NPD6015	Approved
0.6693	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD5988	Approved
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6585	Remote Similarity	NPD6053	Discontinued
0.6583	Remote Similarity	NPD5697	Approved
0.6583	Remote Similarity	NPD5701	Approved
0.6581	Remote Similarity	NPD4159	Approved
0.6577	Remote Similarity	NPD6051	Approved
0.6571	Remote Similarity	NPD6929	Approved
0.6571	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD6921	Approved
0.6557	Remote Similarity	NPD6883	Approved
0.6557	Remote Similarity	NPD7102	Approved
0.6557	Remote Similarity	NPD6371	Approved
0.6557	Remote Similarity	NPD7290	Approved
0.6549	Remote Similarity	NPD6399	Phase 3
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3168	Discontinued
0.6509	Remote Similarity	NPD7332	Phase 2
0.6509	Remote Similarity	NPD7514	Phase 3
0.6504	Remote Similarity	NPD6869	Approved
0.6504	Remote Similarity	NPD6617	Approved
0.6504	Remote Similarity	NPD6847	Approved
0.6504	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD6008	Approved
0.6491	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7900	Approved
0.6475	Remote Similarity	NPD6013	Approved
0.6475	Remote Similarity	NPD6012	Approved
0.6475	Remote Similarity	NPD6014	Approved
0.6466	Remote Similarity	NPD6083	Phase 2
0.6466	Remote Similarity	NPD6084	Phase 2
0.6462	Remote Similarity	NPD7604	Phase 2
0.6462	Remote Similarity	NPD6067	Discontinued
0.646	Remote Similarity	NPD7087	Discontinued
0.646	Remote Similarity	NPD7983	Approved
0.6446	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6933	Approved
0.6434	Remote Similarity	NPD5983	Phase 2
0.6404	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD5779	Approved
0.6393	Remote Similarity	NPD6011	Approved
0.6391	Remote Similarity	NPD6033	Approved
0.6389	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5776	Phase 2
0.6381	Remote Similarity	NPD6925	Approved
0.6381	Remote Similarity	NPD6932	Approved
0.6371	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7260	Phase 2
0.6364	Remote Similarity	NPD6640	Phase 3
0.6364	Remote Similarity	NPD6893	Approved
0.6364	Remote Similarity	NPD6336	Discontinued
0.6325	Remote Similarity	NPD4755	Approved
0.6321	Remote Similarity	NPD7145	Approved
0.6316	Remote Similarity	NPD8034	Phase 2
0.6316	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD8035	Phase 2
0.6306	Remote Similarity	NPD3618	Phase 1
0.6296	Remote Similarity	NPD6898	Phase 1
0.6296	Remote Similarity	NPD6902	Approved
0.629	Remote Similarity	NPD4634	Approved
0.6283	Remote Similarity	NPD5328	Approved
0.6275	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6683	Phase 2
0.6261	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD5126	Approved
0.626	Remote Similarity	NPD5125	Phase 3
0.625	Remote Similarity	NPD6926	Approved
0.625	Remote Similarity	NPD6924	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5286	Approved
0.6218	Remote Similarity	NPD4700	Approved
0.6218	Remote Similarity	NPD4696	Approved
0.6218	Remote Similarity	NPD5285	Approved
0.6216	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7509	Discontinued
0.6195	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7339	Approved
0.619	Remote Similarity	NPD6942	Approved
0.6174	Remote Similarity	NPD6079	Approved
0.6172	Remote Similarity	NPD6274	Approved
0.6161	Remote Similarity	NPD6684	Approved
0.6161	Remote Similarity	NPD6409	Approved
0.6161	Remote Similarity	NPD5330	Approved
0.6161	Remote Similarity	NPD7334	Approved
0.6161	Remote Similarity	NPD7521	Approved
0.6161	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD5141	Approved
0.6143	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6101	Approved
0.614	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5696	Approved
0.6132	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4786	Approved
0.6121	Remote Similarity	NPD8171	Discontinued
0.6116	Remote Similarity	NPD5226	Approved
0.6116	Remote Similarity	NPD4633	Approved
0.6116	Remote Similarity	NPD5224	Approved
0.6116	Remote Similarity	NPD5225	Approved
0.6107	Remote Similarity	NPD7741	Discontinued
0.6098	Remote Similarity	NPD5357	Phase 1
0.6098	Remote Similarity	NPD4767	Approved
0.6098	Remote Similarity	NPD4768	Approved
0.6091	Remote Similarity	NPD3667	Approved
0.609	Remote Similarity	NPD7829	Approved
0.609	Remote Similarity	NPD7830	Approved
0.6087	Remote Similarity	NPD6845	Suspended
0.6087	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6335	Approved
0.6071	Remote Similarity	NPD1694	Approved
0.6066	Remote Similarity	NPD5174	Approved
0.6066	Remote Similarity	NPD5175	Approved
0.6061	Remote Similarity	NPD6909	Approved
0.6061	Remote Similarity	NPD6908	Approved
0.6053	Remote Similarity	NPD6672	Approved
0.6053	Remote Similarity	NPD6903	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