NPASS Compound

Structure

NPC475056 OpenBabel07101718202D 34 38 0 0 1 0 0 0 0 0999 V2000 3.7787 -1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0158 1.5317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3989 -0.8316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3686 0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9292 1.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4478 -1.1407 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3467 0.7885 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6557 -0.1625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6994 0.2533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7213 0.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1861 2.1085 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.6977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5134 -0.5169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 24 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 26 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 15 30 1 0 0 0 0 16 1 1 6 0 0 0 16 21 1 0 0 0 0 17 2 1 1 0 0 0 18 27 1 6 0 0 0 19 31 2 0 0 0 0 20 6 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 17 1 1 0 0 0 22 28 1 6 0 0 0 23 27 1 6 0 0 0 24 28 1 6 0 0 0 24 29 1 0 0 0 0 25 28 1 6 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 33 1 1 0 0 0 27 3 1 6 0 0 0 28 4 1 6 0 0 0 29 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.32
Volume:	515.093
LogP:	5.404
LogD:	4.487
LogS:	-4.528
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	5.292
Fsp3:	0.966
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	1.6031483028200455e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.659
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.833
Plasma Protein Binding (PPB):	94.56256103515625%
Volume Distribution (VD):	1.06
Pgp-substrate:	2.178318500518799%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.255
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.292
CYP3A4-inhibitor:	0.4
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	12.587
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.899
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.538
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.59
Maximum Recommended Daily Dose:	0.606
Skin Sensitization:	0.907
Carcinogencity:	0.549
Eye Corrosion:	0.21
Eye Irritation:	0.056
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC475056

Natural Product ID:	NPC475056
*Common Name:**	Aragusterol C
IUPAC Name:	(5S,8R,9S,10S,12R,13S,14S,17S)-17-[(2S,3R,5R)-1-chloro-2,3-dihydroxy-5-[(1S,2S)-2-methylcyclopropyl]hexan-2-yl]-12-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Aragusterol C
Standard InCHIKey:	IDJFQGHMTPJXRG-ABQXLVMOSA-N
Standard InCHI:	InChI=1S/C29H47ClO4/c1-16-11-21(16)17(2)12-26(33)29(34,15-30)24-8-7-22-20-6-5-18-13-19(31)9-10-27(18,3)23(20)14-25(32)28(22,24)4/h16-18,20-26,32-34H,5-15H2,1-4H3/t16-,17+,18-,20-,21-,22-,23-,24-,25+,26+,27-,28-,29-/m0/s1
SMILES:	CC1CC1C(C)CC(C(CCl)(C2CCC3C2(C(CC4C3CCC5C4(CCC(=O)C5)C)O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494650
PubChem CID:	9848615
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols and derivatives

*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
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11809054]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[16124771]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16378375]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584401]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Maldives	n.a.	PMID[9873492]

☑ 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
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.041	ug.mL-1	PMID[551854]

☑ 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 NPC475056 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	388
0.1-0.2	3837
0.2-0.3	12973
0.3-0.4	11831
0.4-0.5	5624
0.5-0.6	5622
0.6-0.7	2087
0.7-0.8	309
0.8-0.85	23
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8539	High Similarity	NPC202937
0.8488	Intermediate Similarity	NPC469745
0.8452	Intermediate Similarity	NPC475031
0.8427	Intermediate Similarity	NPC476730
0.8276	Intermediate Similarity	NPC12933
0.8235	Intermediate Similarity	NPC264602
0.8222	Intermediate Similarity	NPC476726
0.8222	Intermediate Similarity	NPC476727
0.8214	Intermediate Similarity	NPC273366
0.8182	Intermediate Similarity	NPC121121
0.8161	Intermediate Similarity	NPC470609
0.8132	Intermediate Similarity	NPC263802
0.8022	Intermediate Similarity	NPC472745
0.8022	Intermediate Similarity	NPC80700
0.8022	Intermediate Similarity	NPC472272
0.8	Intermediate Similarity	NPC50438
0.7976	Intermediate Similarity	NPC232112
0.7957	Intermediate Similarity	NPC24705
0.7957	Intermediate Similarity	NPC56962
0.7931	Intermediate Similarity	NPC224802
0.7931	Intermediate Similarity	NPC171426
0.7931	Intermediate Similarity	NPC324700
0.7931	Intermediate Similarity	NPC80089
0.7931	Intermediate Similarity	NPC34046
0.7889	Intermediate Similarity	NPC472744
0.7857	Intermediate Similarity	NPC151018
0.7857	Intermediate Similarity	NPC320549
0.7857	Intermediate Similarity	NPC156277
0.7857	Intermediate Similarity	NPC58057
0.7841	Intermediate Similarity	NPC201276
0.7841	Intermediate Similarity	NPC80891
0.7826	Intermediate Similarity	NPC474448
0.7816	Intermediate Similarity	NPC23884
0.7816	Intermediate Similarity	NPC317913
0.7816	Intermediate Similarity	NPC207010
0.7791	Intermediate Similarity	NPC97534
0.7791	Intermediate Similarity	NPC174964
0.7791	Intermediate Similarity	NPC195155
0.7791	Intermediate Similarity	NPC159789
0.7778	Intermediate Similarity	NPC268040
0.7778	Intermediate Similarity	NPC317066
0.7753	Intermediate Similarity	NPC477851
0.7727	Intermediate Similarity	NPC147993
0.7701	Intermediate Similarity	NPC5767
0.7701	Intermediate Similarity	NPC472487
0.7701	Intermediate Similarity	NPC4209
0.7701	Intermediate Similarity	NPC472486
0.7701	Intermediate Similarity	NPC475742
0.7692	Intermediate Similarity	NPC268578
0.7692	Intermediate Similarity	NPC217559
0.7692	Intermediate Similarity	NPC292458
0.7692	Intermediate Similarity	NPC327451
0.7674	Intermediate Similarity	NPC472854
0.7674	Intermediate Similarity	NPC254340
0.7647	Intermediate Similarity	NPC89310
0.764	Intermediate Similarity	NPC245029
0.764	Intermediate Similarity	NPC287452
0.764	Intermediate Similarity	NPC31302
0.764	Intermediate Similarity	NPC320144
0.7634	Intermediate Similarity	NPC302111
0.7619	Intermediate Similarity	NPC213178
0.7619	Intermediate Similarity	NPC6120
0.7619	Intermediate Similarity	NPC470830
0.7619	Intermediate Similarity	NPC299948
0.7619	Intermediate Similarity	NPC66407
0.7619	Intermediate Similarity	NPC327728
0.7619	Intermediate Similarity	NPC131892
0.7619	Intermediate Similarity	NPC241085
0.7614	Intermediate Similarity	NPC221420
0.7609	Intermediate Similarity	NPC471044
0.7609	Intermediate Similarity	NPC473336
0.7609	Intermediate Similarity	NPC474996
0.7604	Intermediate Similarity	NPC52756
0.7586	Intermediate Similarity	NPC317242
0.7586	Intermediate Similarity	NPC125767
0.7586	Intermediate Similarity	NPC196136
0.7586	Intermediate Similarity	NPC158208
0.7586	Intermediate Similarity	NPC212733
0.7586	Intermediate Similarity	NPC21220
0.7586	Intermediate Similarity	NPC243027
0.7558	Intermediate Similarity	NPC153719
0.7558	Intermediate Similarity	NPC81759
0.7558	Intermediate Similarity	NPC470610
0.7551	Intermediate Similarity	NPC17336
0.7528	Intermediate Similarity	NPC185465
0.75	Intermediate Similarity	NPC163597
0.75	Intermediate Similarity	NPC77756
0.75	Intermediate Similarity	NPC269684
0.7474	Intermediate Similarity	NPC226491
0.7474	Intermediate Similarity	NPC477614
0.7473	Intermediate Similarity	NPC77311
0.7471	Intermediate Similarity	NPC167702
0.7471	Intermediate Similarity	NPC48795
0.7471	Intermediate Similarity	NPC228994
0.7471	Intermediate Similarity	NPC192501
0.7471	Intermediate Similarity	NPC280026
0.7471	Intermediate Similarity	NPC10476
0.7449	Intermediate Similarity	NPC470423
0.7442	Intermediate Similarity	NPC187471
0.7442	Intermediate Similarity	NPC473267
0.7442	Intermediate Similarity	NPC470071
0.7442	Intermediate Similarity	NPC252182
0.7442	Intermediate Similarity	NPC127094
0.7442	Intermediate Similarity	NPC1340
0.7426	Intermediate Similarity	NPC41843
0.7419	Intermediate Similarity	NPC319909
0.7416	Intermediate Similarity	NPC298168
0.7416	Intermediate Similarity	NPC302578
0.7416	Intermediate Similarity	NPC128951
0.7416	Intermediate Similarity	NPC64081
0.7416	Intermediate Similarity	NPC180199
0.7416	Intermediate Similarity	NPC192046
0.7416	Intermediate Similarity	NPC474574
0.7416	Intermediate Similarity	NPC143133
0.7416	Intermediate Similarity	NPC185915
0.7416	Intermediate Similarity	NPC477227
0.7416	Intermediate Similarity	NPC477919
0.7416	Intermediate Similarity	NPC105208
0.7412	Intermediate Similarity	NPC107919
0.74	Intermediate Similarity	NPC170978
0.7396	Intermediate Similarity	NPC61688
0.7391	Intermediate Similarity	NPC60018
0.7391	Intermediate Similarity	NPC289486
0.7391	Intermediate Similarity	NPC475388
0.7391	Intermediate Similarity	NPC328007
0.7391	Intermediate Similarity	NPC202688
0.7391	Intermediate Similarity	NPC30583
0.7391	Intermediate Similarity	NPC61107
0.7391	Intermediate Similarity	NPC154043
0.7386	Intermediate Similarity	NPC24014
0.7386	Intermediate Similarity	NPC27349
0.7356	Intermediate Similarity	NPC472341
0.7356	Intermediate Similarity	NPC310766
0.7356	Intermediate Similarity	NPC473238
0.7347	Intermediate Similarity	NPC291373
0.734	Intermediate Similarity	NPC76518
0.7333	Intermediate Similarity	NPC67657
0.7333	Intermediate Similarity	NPC476732
0.7333	Intermediate Similarity	NPC18857
0.7333	Intermediate Similarity	NPC478128
0.7333	Intermediate Similarity	NPC199965
0.7326	Intermediate Similarity	NPC251201
0.7326	Intermediate Similarity	NPC192192
0.7326	Intermediate Similarity	NPC232925
0.7326	Intermediate Similarity	NPC63588
0.732	Intermediate Similarity	NPC136801
0.732	Intermediate Similarity	NPC46758
0.7312	Intermediate Similarity	NPC111582
0.7312	Intermediate Similarity	NPC477285
0.73	Intermediate Similarity	NPC476728
0.73	Intermediate Similarity	NPC116683
0.7292	Intermediate Similarity	NPC193360
0.7292	Intermediate Similarity	NPC476379
0.7283	Intermediate Similarity	NPC58631
0.7273	Intermediate Similarity	NPC470424
0.7273	Intermediate Similarity	NPC304499
0.7273	Intermediate Similarity	NPC133922
0.7273	Intermediate Similarity	NPC277399
0.7253	Intermediate Similarity	NPC477282
0.7253	Intermediate Similarity	NPC52951
0.7253	Intermediate Similarity	NPC269333
0.7253	Intermediate Similarity	NPC81074
0.7222	Intermediate Similarity	NPC133596
0.7222	Intermediate Similarity	NPC11907
0.7212	Intermediate Similarity	NPC34562
0.7209	Intermediate Similarity	NPC254037
0.7209	Intermediate Similarity	NPC470833
0.7209	Intermediate Similarity	NPC129829
0.7209	Intermediate Similarity	NPC324607
0.7209	Intermediate Similarity	NPC477820
0.7209	Intermediate Similarity	NPC321732
0.7204	Intermediate Similarity	NPC311642
0.7204	Intermediate Similarity	NPC242771
0.7204	Intermediate Similarity	NPC286719
0.7204	Intermediate Similarity	NPC100366
0.7204	Intermediate Similarity	NPC477286
0.7204	Intermediate Similarity	NPC164289
0.72	Intermediate Similarity	NPC470031
0.7191	Intermediate Similarity	NPC91387
0.7191	Intermediate Similarity	NPC270306
0.7191	Intermediate Similarity	NPC231680
0.7188	Intermediate Similarity	NPC469317
0.7188	Intermediate Similarity	NPC239938
0.7188	Intermediate Similarity	NPC469314
0.7188	Intermediate Similarity	NPC138756
0.7188	Intermediate Similarity	NPC241875
0.7184	Intermediate Similarity	NPC477172
0.7176	Intermediate Similarity	NPC475884
0.7176	Intermediate Similarity	NPC473230
0.7174	Intermediate Similarity	NPC261616
0.7174	Intermediate Similarity	NPC472853
0.7174	Intermediate Similarity	NPC16449
0.7172	Intermediate Similarity	NPC472232
0.7172	Intermediate Similarity	NPC476189
0.7172	Intermediate Similarity	NPC472231
0.7159	Intermediate Similarity	NPC282905
0.7159	Intermediate Similarity	NPC477229
0.7159	Intermediate Similarity	NPC68426
0.7159	Intermediate Similarity	NPC474123
0.7158	Intermediate Similarity	NPC266651

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 NPC475056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	3831
0.2-0.3	3530
0.3-0.4	875
0.4-0.5	256
0.5-0.6	197
0.6-0.7	78
0.7-0.8	22
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
0.7931	Intermediate Similarity	NPD6697	Approved
0.7931	Intermediate Similarity	NPD6118	Approved
0.7931	Intermediate Similarity	NPD6115	Approved
0.7931	Intermediate Similarity	NPD6114	Approved
0.7857	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6116	Phase 1
0.7791	Intermediate Similarity	NPD3703	Phase 2
0.7701	Intermediate Similarity	NPD6117	Approved
0.7619	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5360	Phase 3
0.7471	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4244	Approved
0.7326	Intermediate Similarity	NPD4245	Approved
0.7326	Intermediate Similarity	NPD4789	Approved
0.7209	Intermediate Similarity	NPD3698	Phase 2
0.7143	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4758	Discontinued
0.6957	Remote Similarity	NPD3671	Phase 1
0.6957	Remote Similarity	NPD5364	Discontinued
0.6854	Remote Similarity	NPD6081	Approved
0.6818	Remote Similarity	NPD5169	Approved
0.6804	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5215	Approved
0.6757	Remote Similarity	NPD5127	Approved
0.6726	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4224	Phase 2
0.6637	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD6415	Discontinued
0.6607	Remote Similarity	NPD5216	Approved
0.6607	Remote Similarity	NPD5217	Approved
0.6598	Remote Similarity	NPD4788	Approved
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6556	Remote Similarity	NPD4787	Phase 1
0.6552	Remote Similarity	NPD6335	Approved
0.6535	Remote Similarity	NPD5328	Approved
0.6531	Remote Similarity	NPD4786	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6505	Remote Similarity	NPD4202	Approved
0.6496	Remote Similarity	NPD4522	Approved
0.6496	Remote Similarity	NPD7100	Approved
0.6486	Remote Similarity	NPD5168	Approved
0.6486	Remote Similarity	NPD5128	Approved
0.6484	Remote Similarity	NPD5777	Approved
0.6475	Remote Similarity	NPD6033	Approved
0.6458	Remote Similarity	NPD7525	Registered
0.6452	Remote Similarity	NPD3702	Approved
0.6449	Remote Similarity	NPD8418	Phase 2
0.6446	Remote Similarity	NPD6336	Discontinued
0.6415	Remote Similarity	NPD4755	Approved
0.641	Remote Similarity	NPD6313	Approved
0.641	Remote Similarity	NPD6314	Approved
0.6408	Remote Similarity	NPD6079	Approved
0.64	Remote Similarity	NPD3618	Phase 1
0.6372	Remote Similarity	NPD4634	Approved
0.6356	Remote Similarity	NPD7101	Approved
0.6327	Remote Similarity	NPD3667	Approved
0.6325	Remote Similarity	NPD6009	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD4700	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6289	Remote Similarity	NPD6928	Phase 2
0.6239	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD6399	Phase 3
0.619	Remote Similarity	NPD5133	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5211	Phase 2
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6168	Remote Similarity	NPD5221	Approved
0.6168	Remote Similarity	NPD4697	Phase 3
0.6168	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5222	Approved
0.6161	Remote Similarity	NPD7128	Approved
0.6161	Remote Similarity	NPD5739	Approved
0.6161	Remote Similarity	NPD6675	Approved
0.6161	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD5174	Approved
0.6126	Remote Similarity	NPD5175	Approved
0.6126	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD5173	Approved
0.6095	Remote Similarity	NPD7515	Phase 2
0.6071	Remote Similarity	NPD5141	Approved
0.6068	Remote Similarity	NPD8133	Approved
0.6058	Remote Similarity	NPD4753	Phase 2
0.6055	Remote Similarity	NPD7638	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7320	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.604	Remote Similarity	NPD3665	Phase 1
0.604	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD3133	Approved
0.6038	Remote Similarity	NPD8171	Discontinued
0.6036	Remote Similarity	NPD5091	Approved
0.6018	Remote Similarity	NPD6920	Discontinued
0.6018	Remote Similarity	NPD4768	Approved
0.6018	Remote Similarity	NPD4767	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5983	Remote Similarity	NPD8297	Approved
0.5966	Remote Similarity	NPD6940	Discontinued
0.5965	Remote Similarity	NPD5701	Approved
0.5965	Remote Similarity	NPD5697	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5946	Remote Similarity	NPD1700	Approved
0.5922	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7115	Discovery
0.5913	Remote Similarity	NPD4729	Approved
0.5913	Remote Similarity	NPD4730	Approved
0.5913	Remote Similarity	NPD6011	Approved
0.5902	Remote Similarity	NPD6054	Approved
0.5902	Remote Similarity	NPD6319	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6649	Approved
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6650	Approved
0.5893	Remote Similarity	NPD7632	Discontinued
0.5882	Remote Similarity	NPD3668	Phase 3
0.5877	Remote Similarity	NPD6008	Approved
0.5862	Remote Similarity	NPD6012	Approved
0.5862	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6013	Approved
0.5859	Remote Similarity	NPD5956	Approved
0.5849	Remote Similarity	NPD6700	Approved
0.5849	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6882	Approved
0.5842	Remote Similarity	NPD4223	Phase 3
0.5842	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD7748	Approved
0.5825	Remote Similarity	NPD5329	Approved
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5818	Remote Similarity	NPD7902	Approved
0.5812	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5249	Phase 3
0.5812	Remote Similarity	NPD5250	Approved
0.5812	Remote Similarity	NPD5248	Approved
0.5812	Remote Similarity	NPD5135	Approved
0.5812	Remote Similarity	NPD5247	Approved
0.5812	Remote Similarity	NPD5251	Approved
0.5806	Remote Similarity	NPD6370	Approved
0.5794	Remote Similarity	NPD7507	Approved
0.5794	Remote Similarity	NPD6702	Approved
0.5794	Remote Similarity	NPD6703	Approved
0.578	Remote Similarity	NPD4629	Approved
0.578	Remote Similarity	NPD5210	Approved
0.578	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5279	Phase 3
0.5758	Remote Similarity	NPD3617	Approved
0.5743	Remote Similarity	NPD4692	Approved
0.5743	Remote Similarity	NPD4139	Approved
0.5728	Remote Similarity	NPD4197	Approved
0.5726	Remote Similarity	NPD6015	Approved
0.5726	Remote Similarity	NPD6016	Approved
0.5714	Remote Similarity	NPD371	Approved
0.5714	Remote Similarity	NPD7492	Approved
0.5703	Remote Similarity	NPD7736	Approved
0.568	Remote Similarity	NPD5988	Approved
0.5678	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5959	Approved
0.5669	Remote Similarity	NPD6616	Approved
0.5667	Remote Similarity	NPD8298	Phase 2
0.5659	Remote Similarity	NPD7319	Approved
0.5625	Remote Similarity	NPD8293	Discontinued
0.5625	Remote Similarity	NPD7078	Approved
0.5619	Remote Similarity	NPD4688	Approved
0.5619	Remote Similarity	NPD5205	Approved
0.5619	Remote Similarity	NPD4693	Phase 3
0.5619	Remote Similarity	NPD4690	Approved
0.5619	Remote Similarity	NPD4138	Approved
0.5619	Remote Similarity	NPD4689	Approved
0.5618	Remote Similarity	NPD3198	Approved
0.5612	Remote Similarity	NPD6942	Approved
0.5612	Remote Similarity	NPD7339	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