NPASS Compound

Structure

NPC473719 OpenBabel07101719142D 37 41 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 -3.7160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0704 -0.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4376 0.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3577 -0.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0013 -0.3211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3685 1.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2086 -1.4171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1294 -2.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2886 -0.0629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1503 0.6677 0.0000 C 0 0 0 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 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2778 -1.7824 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 -0.5075 -2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 -1.5243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 -7.0812 1.0331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1287 -2.7713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 -2.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4959 -1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 16 2 0 0 0 0 6 9 2 0 0 0 0 6 16 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 1 1 1 0 0 0 14 18 1 0 0 0 0 15 2 1 1 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 6 0 0 0 19 28 1 1 0 0 0 20 27 1 0 0 0 0 20 31 1 1 0 0 0 21 28 1 1 0 0 0 21 36 1 0 0 0 0 22 32 2 0 0 0 0 22 37 1 0 0 0 0 23 33 2 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 34 2 0 0 0 0 25 26 1 0 0 0 0 25 37 1 1 0 0 0 26 28 1 6 0 0 0 26 29 1 0 0 0 0 27 29 1 0 0 0 0 27 35 2 0 0 0 0 28 3 1 6 0 0 0 29 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.23
Volume:	516.588
LogP:	3.356
LogD:	1.683
LogS:	-3.511
# Rotatable Bonds:	4
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	5.129
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
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:	-5.256
MDCK Permeability:	4.295405597076751e-05
Pgp-inhibitor:	0.152
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.89
Plasma Protein Binding (PPB):	91.32695770263672%
Volume Distribution (VD):	0.685
Pgp-substrate:	9.435611724853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.339
CYP2C9-inhibitor:	0.333
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	16.508
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.217
Human Hepatotoxicity (H-HT):	0.487
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.431
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.297
Carcinogencity:	0.395
Eye Corrosion:	0.186
Eye Irritation:	0.022
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC473719

Natural Product ID:	NPC473719
*Common Name:**	NHJGRRIDYNHGNT-RBASVOMWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NHJGRRIDYNHGNT-RBASVOMWSA-N
Standard InCHI:	InChI=1S/C29H34O8/c1-14-11-20(31)27(35)29(4)18(14)12-21-28(3)19(13-23(33)36-21)15(2)24(34)25(26(28)29)37-22(32)10-7-16-5-8-17(30)9-6-16/h5-10,14-15,18-21,25-26,30-31H,11-13H2,1-4H3/b10-7+/t14-,15-,18+,19+,20+,21-,25-,26+,28-,29+/m1/s1
SMILES:	CC1CC(C(=O)C2(C1CC3C4(C2C(C(=O)C(C4CC(=O)O3)C)OC(=O)C=CC5=CC=C(C=C5)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450181
PubChem CID:	10255768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO18703	Castela texana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984156]
NPO18703	Castela texana	Species	Simaroubaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.92	ug.mL-1	PMID[531237]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.75	ug.mL-1	PMID[531237]

☑ 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 NPC473719 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	344
0.1-0.2	1288
0.2-0.3	2676
0.3-0.4	5074
0.4-0.5	9515
0.5-0.6	10220
0.6-0.7	10807
0.7-0.8	2630
0.8-0.85	102
0.85-0.9	40
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8897	High Similarity	NPC172311
0.875	High Similarity	NPC249817
0.8733	High Similarity	NPC477483
0.8733	High Similarity	NPC325032
0.869	High Similarity	NPC22676
0.869	High Similarity	NPC198621
0.869	High Similarity	NPC475482
0.869	High Similarity	NPC216940
0.8681	High Similarity	NPC173569
0.8681	High Similarity	NPC477874
0.8675	High Similarity	NPC279442
0.8618	High Similarity	NPC327962
0.8609	High Similarity	NPC5568
0.8591	High Similarity	NPC25491
0.8542	High Similarity	NPC18982
0.8542	High Similarity	NPC475346
0.8542	High Similarity	NPC475627
0.8542	High Similarity	NPC475457
0.8514	High Similarity	NPC304110
0.8514	High Similarity	NPC27518
0.8514	High Similarity	NPC472801
0.8506	High Similarity	NPC48671
0.8503	High Similarity	NPC248287
0.8503	High Similarity	NPC234548
0.8483	Intermediate Similarity	NPC194970
0.8462	Intermediate Similarity	NPC472807
0.8438	Intermediate Similarity	NPC161151
0.8425	Intermediate Similarity	NPC279463
0.8421	Intermediate Similarity	NPC470330
0.8418	Intermediate Similarity	NPC471750
0.8377	Intermediate Similarity	NPC116292
0.8377	Intermediate Similarity	NPC179128
0.8377	Intermediate Similarity	NPC87630
0.8377	Intermediate Similarity	NPC267469
0.8369	Intermediate Similarity	NPC137416
0.8313	Intermediate Similarity	NPC266365
0.8289	Intermediate Similarity	NPC169942
0.8289	Intermediate Similarity	NPC53520
0.8278	Intermediate Similarity	NPC477873
0.8278	Intermediate Similarity	NPC469447
0.8267	Intermediate Similarity	NPC3218
0.8264	Intermediate Similarity	NPC86257
0.8261	Intermediate Similarity	NPC315772
0.8258	Intermediate Similarity	NPC35160
0.8258	Intermediate Similarity	NPC162569
0.8235	Intermediate Similarity	NPC208293
0.8231	Intermediate Similarity	NPC11266
0.8221	Intermediate Similarity	NPC469419
0.8219	Intermediate Similarity	NPC323379
0.8219	Intermediate Similarity	NPC327204
0.8217	Intermediate Similarity	NPC266084
0.8217	Intermediate Similarity	NPC475162
0.8217	Intermediate Similarity	NPC475216
0.8217	Intermediate Similarity	NPC475145
0.8217	Intermediate Similarity	NPC475595
0.8217	Intermediate Similarity	NPC473544
0.8217	Intermediate Similarity	NPC83663
0.8205	Intermediate Similarity	NPC119252
0.8205	Intermediate Similarity	NPC261659
0.8204	Intermediate Similarity	NPC475613
0.8193	Intermediate Similarity	NPC124828
0.8188	Intermediate Similarity	NPC475957
0.8188	Intermediate Similarity	NPC471152
0.8182	Intermediate Similarity	NPC81698
0.8182	Intermediate Similarity	NPC250046
0.8182	Intermediate Similarity	NPC51513
0.8182	Intermediate Similarity	NPC474991
0.8182	Intermediate Similarity	NPC193698
0.8182	Intermediate Similarity	NPC60509
0.8182	Intermediate Similarity	NPC202112
0.8176	Intermediate Similarity	NPC471968
0.8176	Intermediate Similarity	NPC472804
0.8169	Intermediate Similarity	NPC265413
0.8169	Intermediate Similarity	NPC10154
0.8163	Intermediate Similarity	NPC19719
0.8163	Intermediate Similarity	NPC477281
0.8163	Intermediate Similarity	NPC49742
0.8163	Intermediate Similarity	NPC477280
0.8158	Intermediate Similarity	NPC204644
0.8146	Intermediate Similarity	NPC182869
0.8141	Intermediate Similarity	NPC247219
0.8133	Intermediate Similarity	NPC283560
0.8133	Intermediate Similarity	NPC139243
0.8133	Intermediate Similarity	NPC116742
0.8133	Intermediate Similarity	NPC24295
0.8129	Intermediate Similarity	NPC161239
0.8129	Intermediate Similarity	NPC198455
0.8129	Intermediate Similarity	NPC165260
0.8129	Intermediate Similarity	NPC7095
0.8121	Intermediate Similarity	NPC266545
0.8121	Intermediate Similarity	NPC202428
0.8117	Intermediate Similarity	NPC75295
0.8117	Intermediate Similarity	NPC8102
0.8117	Intermediate Similarity	NPC66894
0.811	Intermediate Similarity	NPC200726
0.8108	Intermediate Similarity	NPC477893
0.8098	Intermediate Similarity	NPC475779
0.8092	Intermediate Similarity	NPC477277
0.8092	Intermediate Similarity	NPC477278
0.8089	Intermediate Similarity	NPC140133
0.8089	Intermediate Similarity	NPC242262
0.8089	Intermediate Similarity	NPC265395
0.8089	Intermediate Similarity	NPC472005
0.8089	Intermediate Similarity	NPC473414
0.8089	Intermediate Similarity	NPC249471
0.8089	Intermediate Similarity	NPC237549
0.8089	Intermediate Similarity	NPC256142
0.8089	Intermediate Similarity	NPC304876
0.8089	Intermediate Similarity	NPC472030
0.8089	Intermediate Similarity	NPC472022
0.8089	Intermediate Similarity	NPC1173
0.8089	Intermediate Similarity	NPC257213
0.8089	Intermediate Similarity	NPC158333
0.8086	Intermediate Similarity	NPC477627
0.8079	Intermediate Similarity	NPC470616
0.8079	Intermediate Similarity	NPC470617
0.8077	Intermediate Similarity	NPC146388
0.8077	Intermediate Similarity	NPC101043
0.8077	Intermediate Similarity	NPC94781
0.8077	Intermediate Similarity	NPC306799
0.8075	Intermediate Similarity	NPC314795
0.8072	Intermediate Similarity	NPC472803
0.8067	Intermediate Similarity	NPC477592
0.8063	Intermediate Similarity	NPC474861
0.8063	Intermediate Similarity	NPC10945
0.8061	Intermediate Similarity	NPC177362
0.8054	Intermediate Similarity	NPC233350
0.8054	Intermediate Similarity	NPC182217
0.8054	Intermediate Similarity	NPC70680
0.8042	Intermediate Similarity	NPC474532
0.8041	Intermediate Similarity	NPC126516
0.8041	Intermediate Similarity	NPC48929
0.8041	Intermediate Similarity	NPC329913
0.8038	Intermediate Similarity	NPC228204
0.8038	Intermediate Similarity	NPC112523
0.8038	Intermediate Similarity	NPC26033
0.8038	Intermediate Similarity	NPC114410
0.8027	Intermediate Similarity	NPC18798
0.8026	Intermediate Similarity	NPC477279
0.8025	Intermediate Similarity	NPC120171
0.8025	Intermediate Similarity	NPC146014
0.8025	Intermediate Similarity	NPC44378
0.8025	Intermediate Similarity	NPC474310
0.8025	Intermediate Similarity	NPC280753
0.8025	Intermediate Similarity	NPC472939
0.8013	Intermediate Similarity	NPC119767
0.8013	Intermediate Similarity	NPC112216
0.8013	Intermediate Similarity	NPC472135
0.8013	Intermediate Similarity	NPC127046
0.8013	Intermediate Similarity	NPC182249
0.8012	Intermediate Similarity	NPC54903
0.8012	Intermediate Similarity	NPC286074
0.8	Intermediate Similarity	NPC84786
0.8	Intermediate Similarity	NPC149002
0.8	Intermediate Similarity	NPC85047
0.8	Intermediate Similarity	NPC88176
0.8	Intermediate Similarity	NPC469396
0.8	Intermediate Similarity	NPC469458
0.8	Intermediate Similarity	NPC159692
0.8	Intermediate Similarity	NPC320734
0.8	Intermediate Similarity	NPC120857
0.8	Intermediate Similarity	NPC212808
0.8	Intermediate Similarity	NPC17274
0.8	Intermediate Similarity	NPC258856
0.7988	Intermediate Similarity	NPC469395
0.7988	Intermediate Similarity	NPC471861
0.7987	Intermediate Similarity	NPC474599
0.7987	Intermediate Similarity	NPC474533
0.7987	Intermediate Similarity	NPC477207
0.7987	Intermediate Similarity	NPC100242
0.7987	Intermediate Similarity	NPC127857
0.7987	Intermediate Similarity	NPC477896
0.7987	Intermediate Similarity	NPC474534
0.7987	Intermediate Similarity	NPC106895
0.7987	Intermediate Similarity	NPC68517
0.7976	Intermediate Similarity	NPC471871
0.7975	Intermediate Similarity	NPC315520
0.7975	Intermediate Similarity	NPC473579
0.7975	Intermediate Similarity	NPC77719
0.7975	Intermediate Similarity	NPC475311
0.7975	Intermediate Similarity	NPC118033
0.7975	Intermediate Similarity	NPC473680
0.7975	Intermediate Similarity	NPC475454
0.7974	Intermediate Similarity	NPC272907
0.7974	Intermediate Similarity	NPC477894
0.7974	Intermediate Similarity	NPC2681
0.7973	Intermediate Similarity	NPC165612
0.7964	Intermediate Similarity	NPC478021
0.7963	Intermediate Similarity	NPC326084
0.7962	Intermediate Similarity	NPC477206
0.7962	Intermediate Similarity	NPC253591
0.7962	Intermediate Similarity	NPC46549
0.7962	Intermediate Similarity	NPC471103
0.7962	Intermediate Similarity	NPC264229
0.7961	Intermediate Similarity	NPC271494
0.7961	Intermediate Similarity	NPC471875
0.7961	Intermediate Similarity	NPC155192
0.7961	Intermediate Similarity	NPC473591
0.7959	Intermediate Similarity	NPC163169
0.7959	Intermediate Similarity	NPC123

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 NPC473719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	847
0.2-0.3	1584
0.3-0.4	2719
0.4-0.5	2096
0.5-0.6	1206
0.6-0.7	376
0.7-0.8	32
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
0.8212	Intermediate Similarity	NPD8166	Discontinued
0.7922	Intermediate Similarity	NPD6190	Approved
0.7756	Intermediate Similarity	NPD7236	Approved
0.7688	Intermediate Similarity	NPD7458	Discontinued
0.7688	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6663	Approved
0.7651	Intermediate Similarity	NPD8127	Discontinued
0.7644	Intermediate Similarity	NPD8150	Discontinued
0.7635	Intermediate Similarity	NPD5736	Approved
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7625	Intermediate Similarity	NPD7239	Suspended
0.7576	Intermediate Similarity	NPD7075	Discontinued
0.7561	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7003	Approved
0.7515	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6273	Approved
0.7485	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD3764	Approved
0.7469	Intermediate Similarity	NPD3226	Approved
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.7405	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7819	Suspended
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7355	Intermediate Similarity	NPD7097	Phase 1
0.7337	Intermediate Similarity	NPD6959	Discontinued
0.7329	Intermediate Similarity	NPD3019	Approved
0.7326	Intermediate Similarity	NPD7228	Approved
0.7325	Intermediate Similarity	NPD7266	Discontinued
0.7317	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD8319	Approved
0.7312	Intermediate Similarity	NPD8320	Phase 1
0.731	Intermediate Similarity	NPD9545	Approved
0.7305	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5844	Phase 1
0.7283	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7473	Discontinued
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6100	Approved
0.7261	Intermediate Similarity	NPD6099	Approved
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7229	Intermediate Similarity	NPD37	Approved
0.7229	Intermediate Similarity	NPD6801	Discontinued
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7225	Intermediate Similarity	NPD7799	Discontinued
0.7212	Intermediate Similarity	NPD6599	Discontinued
0.7211	Intermediate Similarity	NPD2932	Approved
0.7209	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6166	Phase 2
0.7209	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7057	Phase 3
0.7202	Intermediate Similarity	NPD7058	Phase 2
0.7202	Intermediate Similarity	NPD4967	Phase 2
0.7202	Intermediate Similarity	NPD4965	Approved
0.7202	Intermediate Similarity	NPD4966	Approved
0.7197	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8455	Phase 2
0.7161	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7390	Discontinued
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7118	Intermediate Similarity	NPD6234	Discontinued
0.7117	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6534	Approved
0.7104	Intermediate Similarity	NPD6535	Approved
0.7101	Intermediate Similarity	NPD7768	Phase 2
0.7097	Intermediate Similarity	NPD7961	Discontinued
0.7097	Intermediate Similarity	NPD8032	Phase 2
0.7093	Intermediate Similarity	NPD6232	Discontinued
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD3750	Approved
0.7081	Intermediate Similarity	NPD7700	Phase 2
0.7081	Intermediate Similarity	NPD7699	Phase 2
0.7078	Intermediate Similarity	NPD7095	Approved
0.7062	Intermediate Similarity	NPD6764	Approved
0.7062	Intermediate Similarity	NPD6765	Approved
0.7062	Intermediate Similarity	NPD7251	Discontinued
0.7059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4140	Approved
0.7051	Intermediate Similarity	NPD4060	Phase 1
0.7041	Intermediate Similarity	NPD5402	Approved
0.7039	Intermediate Similarity	NPD1470	Approved
0.7034	Intermediate Similarity	NPD2629	Approved
0.7032	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7874	Approved
0.7022	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7808	Phase 3
0.7018	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2532	Approved
0.7012	Intermediate Similarity	NPD2533	Approved
0.7012	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2534	Approved
0.7006	Intermediate Similarity	NPD6797	Phase 2
0.7006	Intermediate Similarity	NPD230	Phase 1
0.7005	Intermediate Similarity	NPD6777	Approved
0.7005	Intermediate Similarity	NPD6778	Approved
0.7005	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD6781	Approved
0.7005	Intermediate Similarity	NPD6782	Approved
0.7005	Intermediate Similarity	NPD6780	Approved
0.7005	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD5763	Approved
0.6987	Remote Similarity	NPD6233	Phase 2
0.6984	Remote Similarity	NPD7696	Phase 3
0.6984	Remote Similarity	NPD7697	Approved
0.6984	Remote Similarity	NPD7698	Approved
0.6982	Remote Similarity	NPD5761	Phase 2
0.6982	Remote Similarity	NPD5760	Phase 2
0.6982	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2799	Discontinued
0.6968	Remote Similarity	NPD7008	Discontinued
0.6966	Remote Similarity	NPD7240	Approved
0.6966	Remote Similarity	NPD7685	Pre-registration
0.6966	Remote Similarity	NPD8368	Discontinued
0.6961	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3091	Approved
0.6959	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1549	Phase 2
0.6954	Remote Similarity	NPD1608	Approved
0.6951	Remote Similarity	NPD6799	Approved
0.6951	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7074	Phase 3
0.6947	Remote Similarity	NPD7870	Phase 2
0.6947	Remote Similarity	NPD7871	Phase 2
0.6941	Remote Similarity	NPD3817	Phase 2
0.6937	Remote Similarity	NPD2935	Discontinued
0.6935	Remote Similarity	NPD8485	Approved
0.6933	Remote Similarity	NPD3026	Approved
0.6933	Remote Similarity	NPD3023	Approved
0.6928	Remote Similarity	NPD3094	Phase 2
0.6928	Remote Similarity	NPD5403	Approved
0.6913	Remote Similarity	NPD3025	Approved
0.6913	Remote Similarity	NPD3024	Approved
0.6909	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6784	Approved
0.6906	Remote Similarity	NPD6785	Approved
0.6897	Remote Similarity	NPD7229	Phase 3
0.6894	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7054	Approved
0.6887	Remote Similarity	NPD1201	Approved
0.6887	Remote Similarity	NPD3092	Approved
0.6885	Remote Similarity	NPD8361	Approved
0.6885	Remote Similarity	NPD8435	Approved
0.6885	Remote Similarity	NPD8360	Approved
0.6875	Remote Similarity	NPD1510	Phase 2
0.6875	Remote Similarity	NPD7033	Discontinued
0.6871	Remote Similarity	NPD4198	Discontinued
0.6864	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1283	Approved
0.6859	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7472	Approved
0.6851	Remote Similarity	NPD8407	Phase 2
0.6842	Remote Similarity	NPD3972	Approved
0.6839	Remote Similarity	NPD7701	Phase 2
0.6836	Remote Similarity	NPD7177	Discontinued
0.6835	Remote Similarity	NPD2979	Phase 3
0.6825	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1934	Approved
0.6821	Remote Similarity	NPD7801	Approved
0.6818	Remote Similarity	NPD3266	Approved
0.6818	Remote Similarity	NPD2797	Approved
0.6818	Remote Similarity	NPD3267	Approved
0.6815	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5401	Approved
0.6807	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7497	Discontinued
0.6804	Remote Similarity	NPD8151	Discontinued
0.6802	Remote Similarity	NPD3882	Suspended
0.68	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4908	Phase 1
0.6792	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5124	Phase 1
0.679	Remote Similarity	NPD6002	Phase 3
0.679	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1471	Phase 3
0.679	Remote Similarity	NPD6005	Phase 3
0.679	Remote Similarity	NPD6004	Phase 3
0.6784	Remote Similarity	NPD1465	Phase 2
0.6782	Remote Similarity	NPD5494	Approved
0.6778	Remote Similarity	NPD5039	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