NPASS Compound

Structure

NPC472309 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 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 2.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 4 1 1 0 0 0 11 12 1 0 0 0 0 12 20 2 0 0 0 0 13 17 1 6 0 0 0 13 19 1 0 0 0 0 14 17 1 6 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 1 0 0 0 19 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.18
Volume:	330.206
LogP:	1.963
LogD:	1.024
LogS:	-3.576
# Rotatable Bonds:	1
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	5.525
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.192
MDCK Permeability:	2.0876712369499728e-05
Pgp-inhibitor:	0.854
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.317

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	64.41961669921875%
Volume Distribution (VD):	0.301
Pgp-substrate:	25.847192764282227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.619
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	2.216
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.103
Carcinogencity:	0.47
Eye Corrosion:	0.819
Eye Irritation:	0.254
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC472309

Natural Product ID:	NPC472309
*Common Name:**	URXWRRMPTDVQFJ-YUVBWEOUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	URXWRRMPTDVQFJ-YUVBWEOUSA-N
Standard InCHI:	InChI=1S/C19H26O4/c1-17-6-3-7-18(2,16(22)23)14(17)8-15(21)19-9-11(12(20)10-19)4-5-13(17)19/h11,13-14H,3-10H2,1-2H3,(H,22,23)/t11-,13+,14+,17+,18-,19-/m1/s1
SMILES:	CC12CCCC(C1CC(=O)C34C2CCC(C3)C(=O)C4)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358083
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones

*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
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	Root Bark	n.a.	n.a.	PMID[25338180]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	1.0	nM	PMID[492830]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	>	10000.0	nM	PMID[492830]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	2.0	nM	PMID[492830]

☑ 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 NPC472309 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	308
0.1-0.2	3505
0.2-0.3	15559
0.3-0.4	9424
0.4-0.5	6382
0.5-0.6	5060
0.6-0.7	2038
0.7-0.8	342
0.8-0.85	56
0.85-0.9	18
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC470956
0.9286	High Similarity	NPC472311
0.9091	High Similarity	NPC469791
0.8955	High Similarity	NPC268736
0.8955	High Similarity	NPC477931
0.8784	High Similarity	NPC472310
0.8714	High Similarity	NPC108131
0.8676	High Similarity	NPC42060
0.8571	High Similarity	NPC474962
0.8571	High Similarity	NPC196197
0.8551	High Similarity	NPC130459
0.8551	High Similarity	NPC474221
0.8551	High Similarity	NPC478180
0.8442	Intermediate Similarity	NPC30583
0.84	Intermediate Similarity	NPC185465
0.8333	Intermediate Similarity	NPC469940
0.831	Intermediate Similarity	NPC252032
0.831	Intermediate Similarity	NPC64466
0.831	Intermediate Similarity	NPC469941
0.831	Intermediate Similarity	NPC319671
0.831	Intermediate Similarity	NPC476734
0.8289	Intermediate Similarity	NPC320144
0.8267	Intermediate Similarity	NPC477918
0.8194	Intermediate Similarity	NPC477850
0.8194	Intermediate Similarity	NPC477929
0.8169	Intermediate Similarity	NPC100917
0.8169	Intermediate Similarity	NPC473225
0.8169	Intermediate Similarity	NPC281203
0.8169	Intermediate Similarity	NPC31187
0.8169	Intermediate Similarity	NPC469724
0.8133	Intermediate Similarity	NPC4209
0.8108	Intermediate Similarity	NPC167702
0.8108	Intermediate Similarity	NPC133922
0.8108	Intermediate Similarity	NPC477930
0.8108	Intermediate Similarity	NPC280026
0.8026	Intermediate Similarity	NPC212661
0.8026	Intermediate Similarity	NPC169389
0.8026	Intermediate Similarity	NPC477919
0.8026	Intermediate Similarity	NPC180199
0.8026	Intermediate Similarity	NPC471035
0.8026	Intermediate Similarity	NPC207010
0.8026	Intermediate Similarity	NPC317913
0.8	Intermediate Similarity	NPC179858
0.8	Intermediate Similarity	NPC132064
0.8	Intermediate Similarity	NPC212733
0.8	Intermediate Similarity	NPC477934
0.7975	Intermediate Similarity	NPC289486
0.7975	Intermediate Similarity	NPC61107
0.7973	Intermediate Similarity	NPC310766
0.7973	Intermediate Similarity	NPC161187
0.7973	Intermediate Similarity	NPC244708
0.7973	Intermediate Similarity	NPC330659
0.7973	Intermediate Similarity	NPC177826
0.7949	Intermediate Similarity	NPC472853
0.7945	Intermediate Similarity	NPC476731
0.7922	Intermediate Similarity	NPC224802
0.7922	Intermediate Similarity	NPC199965
0.7922	Intermediate Similarity	NPC34046
0.7922	Intermediate Similarity	NPC476732
0.7922	Intermediate Similarity	NPC80089
0.7922	Intermediate Similarity	NPC171426
0.7922	Intermediate Similarity	NPC324700
0.7922	Intermediate Similarity	NPC329117
0.7901	Intermediate Similarity	NPC473038
0.7895	Intermediate Similarity	NPC246445
0.7895	Intermediate Similarity	NPC477933
0.7895	Intermediate Similarity	NPC477932
0.7895	Intermediate Similarity	NPC471046
0.7875	Intermediate Similarity	NPC472847
0.7838	Intermediate Similarity	NPC58057
0.7838	Intermediate Similarity	NPC473267
0.7838	Intermediate Similarity	NPC197701
0.7838	Intermediate Similarity	NPC151018
0.7838	Intermediate Similarity	NPC320549
0.7838	Intermediate Similarity	NPC156277
0.7821	Intermediate Similarity	NPC80891
0.7821	Intermediate Similarity	NPC192744
0.7821	Intermediate Similarity	NPC201276
0.7808	Intermediate Similarity	NPC131892
0.7808	Intermediate Similarity	NPC6120
0.7808	Intermediate Similarity	NPC324607
0.7808	Intermediate Similarity	NPC327728
0.7808	Intermediate Similarity	NPC213178
0.7808	Intermediate Similarity	NPC321732
0.7792	Intermediate Similarity	NPC474404
0.7792	Intermediate Similarity	NPC66105
0.7792	Intermediate Similarity	NPC143133
0.7792	Intermediate Similarity	NPC112463
0.7792	Intermediate Similarity	NPC298168
0.7763	Intermediate Similarity	NPC21220
0.7763	Intermediate Similarity	NPC125767
0.7746	Intermediate Similarity	NPC230047
0.7746	Intermediate Similarity	NPC19311
0.7733	Intermediate Similarity	NPC232112
0.7722	Intermediate Similarity	NPC477851
0.7722	Intermediate Similarity	NPC261616
0.7683	Intermediate Similarity	NPC62572
0.7671	Intermediate Similarity	NPC474954
0.7662	Intermediate Similarity	NPC472486
0.7662	Intermediate Similarity	NPC472487
0.7662	Intermediate Similarity	NPC5767
0.7662	Intermediate Similarity	NPC475742
0.7632	Intermediate Similarity	NPC472854
0.7632	Intermediate Similarity	NPC254340
0.7625	Intermediate Similarity	NPC12933
0.76	Intermediate Similarity	NPC89310
0.76	Intermediate Similarity	NPC478227
0.76	Intermediate Similarity	NPC290058
0.7568	Intermediate Similarity	NPC295788
0.7564	Intermediate Similarity	NPC68828
0.7564	Intermediate Similarity	NPC74685
0.7564	Intermediate Similarity	NPC221420
0.7564	Intermediate Similarity	NPC238227
0.7564	Intermediate Similarity	NPC264602
0.7561	Intermediate Similarity	NPC209882
0.7561	Intermediate Similarity	NPC319909
0.7561	Intermediate Similarity	NPC473336
0.7561	Intermediate Similarity	NPC471044
0.7534	Intermediate Similarity	NPC41542
0.7532	Intermediate Similarity	NPC174964
0.7532	Intermediate Similarity	NPC97534
0.7532	Intermediate Similarity	NPC273366
0.7532	Intermediate Similarity	NPC195155
0.7532	Intermediate Similarity	NPC159789
0.7531	Intermediate Similarity	NPC477935
0.7531	Intermediate Similarity	NPC328007
0.7531	Intermediate Similarity	NPC477936
0.7531	Intermediate Similarity	NPC121121
0.75	Intermediate Similarity	NPC248567
0.747	Intermediate Similarity	NPC224345
0.747	Intermediate Similarity	NPC201655
0.7468	Intermediate Similarity	NPC26029
0.7468	Intermediate Similarity	NPC476810
0.7439	Intermediate Similarity	NPC471037
0.7439	Intermediate Similarity	NPC259173
0.7439	Intermediate Similarity	NPC472740
0.7436	Intermediate Similarity	NPC20466
0.7432	Intermediate Similarity	NPC2568
0.7432	Intermediate Similarity	NPC260319
0.7432	Intermediate Similarity	NPC103647
0.7432	Intermediate Similarity	NPC180777
0.7407	Intermediate Similarity	NPC58631
0.7407	Intermediate Similarity	NPC147066
0.7403	Intermediate Similarity	NPC317212
0.7381	Intermediate Similarity	NPC120395
0.7381	Intermediate Similarity	NPC472272
0.7381	Intermediate Similarity	NPC70661
0.7381	Intermediate Similarity	NPC248216
0.7381	Intermediate Similarity	NPC92139
0.7381	Intermediate Similarity	NPC302111
0.7375	Intermediate Similarity	NPC52951
0.7368	Intermediate Similarity	NPC126642
0.7361	Intermediate Similarity	NPC128608
0.7353	Intermediate Similarity	NPC143597
0.7353	Intermediate Similarity	NPC151464
0.7342	Intermediate Similarity	NPC23884
0.7342	Intermediate Similarity	NPC106078
0.7342	Intermediate Similarity	NPC475031
0.7317	Intermediate Similarity	NPC133391
0.7317	Intermediate Similarity	NPC317066
0.7317	Intermediate Similarity	NPC170985
0.7317	Intermediate Similarity	NPC271163
0.7313	Intermediate Similarity	NPC53245
0.7313	Intermediate Similarity	NPC288296
0.7308	Intermediate Similarity	NPC27349
0.7308	Intermediate Similarity	NPC201027
0.7308	Intermediate Similarity	NPC24014
0.7303	Intermediate Similarity	NPC266431
0.7284	Intermediate Similarity	NPC470609
0.7284	Intermediate Similarity	NPC1882
0.7273	Intermediate Similarity	NPC36310
0.7273	Intermediate Similarity	NPC279241
0.7273	Intermediate Similarity	NPC475230
0.7262	Intermediate Similarity	NPC311702
0.7262	Intermediate Similarity	NPC94531
0.7262	Intermediate Similarity	NPC123319
0.7262	Intermediate Similarity	NPC142649
0.725	Intermediate Similarity	NPC243594
0.725	Intermediate Similarity	NPC472608
0.725	Intermediate Similarity	NPC321690
0.725	Intermediate Similarity	NPC31031
0.725	Intermediate Similarity	NPC63020
0.7241	Intermediate Similarity	NPC476296
0.7229	Intermediate Similarity	NPC167103
0.7229	Intermediate Similarity	NPC245866
0.7229	Intermediate Similarity	NPC15821
0.7229	Intermediate Similarity	NPC271784
0.7229	Intermediate Similarity	NPC327451
0.7222	Intermediate Similarity	NPC470387
0.7215	Intermediate Similarity	NPC108840
0.7215	Intermediate Similarity	NPC104806
0.7209	Intermediate Similarity	NPC474719
0.7209	Intermediate Similarity	NPC236459
0.7209	Intermediate Similarity	NPC56413
0.7206	Intermediate Similarity	NPC184819
0.72	Intermediate Similarity	NPC290445
0.72	Intermediate Similarity	NPC36616
0.7195	Intermediate Similarity	NPC38350
0.7195	Intermediate Similarity	NPC221647
0.7195	Intermediate Similarity	NPC472230

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 NPC472309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	3644
0.2-0.3	3574
0.3-0.4	962
0.4-0.5	273
0.5-0.6	231
0.6-0.7	90
0.7-0.8	14
0.8-0.85	13
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD6081	Approved
0.9242	High Similarity	NPD4224	Phase 2
0.8169	Intermediate Similarity	NPD5360	Phase 3
0.8169	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6117	Approved
0.8108	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6116	Phase 1
0.8	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3702	Approved
0.7945	Intermediate Similarity	NPD4789	Approved
0.7922	Intermediate Similarity	NPD6115	Approved
0.7922	Intermediate Similarity	NPD6697	Approved
0.7922	Intermediate Similarity	NPD6118	Approved
0.7922	Intermediate Similarity	NPD6114	Approved
0.7838	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4758	Discontinued
0.7838	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3698	Phase 2
0.7808	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4244	Approved
0.7703	Intermediate Similarity	NPD4245	Approved
0.76	Intermediate Similarity	NPD5777	Approved
0.7532	Intermediate Similarity	NPD3703	Phase 2
0.7468	Intermediate Similarity	NPD5364	Discontinued
0.7313	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3671	Phase 1
0.6966	Remote Similarity	NPD8034	Phase 2
0.6966	Remote Similarity	NPD8035	Phase 2
0.6889	Remote Similarity	NPD6399	Phase 3
0.6829	Remote Similarity	NPD3617	Approved
0.6824	Remote Similarity	NPD4788	Approved
0.6706	Remote Similarity	NPD4221	Approved
0.6706	Remote Similarity	NPD4223	Phase 3
0.6702	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD7614	Phase 1
0.6593	Remote Similarity	NPD5281	Approved
0.6593	Remote Similarity	NPD5284	Approved
0.6588	Remote Similarity	NPD4692	Approved
0.6588	Remote Similarity	NPD4139	Approved
0.6556	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4786	Approved
0.6552	Remote Similarity	NPD4197	Approved
0.6512	Remote Similarity	NPD3667	Approved
0.6477	Remote Similarity	NPD5329	Approved
0.6456	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6672	Approved
0.6444	Remote Similarity	NPD5737	Approved
0.6421	Remote Similarity	NPD6083	Phase 2
0.6421	Remote Similarity	NPD6084	Phase 2
0.6413	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD4690	Approved
0.6404	Remote Similarity	NPD4138	Approved
0.6404	Remote Similarity	NPD4693	Phase 3
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4689	Approved
0.6404	Remote Similarity	NPD6098	Approved
0.6404	Remote Similarity	NPD4688	Approved
0.6404	Remote Similarity	NPD5205	Approved
0.6383	Remote Similarity	NPD5695	Phase 3
0.6383	Remote Similarity	NPD4629	Approved
0.6383	Remote Similarity	NPD5210	Approved
0.6374	Remote Similarity	NPD4753	Phase 2
0.6374	Remote Similarity	NPD6080	Approved
0.6374	Remote Similarity	NPD5328	Approved
0.6374	Remote Similarity	NPD6904	Approved
0.6374	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD634	Phase 3
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6351	Remote Similarity	NPD3198	Approved
0.6338	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4697	Phase 3
0.6289	Remote Similarity	NPD8418	Phase 2
0.6279	Remote Similarity	NPD4695	Discontinued
0.6277	Remote Similarity	NPD7748	Approved
0.6264	Remote Similarity	NPD5208	Approved
0.6264	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7902	Approved
0.6237	Remote Similarity	NPD6079	Approved
0.6237	Remote Similarity	NPD5693	Phase 1
0.6234	Remote Similarity	NPD7909	Approved
0.6222	Remote Similarity	NPD3618	Phase 1
0.6222	Remote Similarity	NPD7521	Approved
0.6222	Remote Similarity	NPD7334	Approved
0.6222	Remote Similarity	NPD6684	Approved
0.6222	Remote Similarity	NPD4694	Approved
0.6222	Remote Similarity	NPD5280	Approved
0.6222	Remote Similarity	NPD5690	Phase 2
0.6222	Remote Similarity	NPD6409	Approved
0.6222	Remote Similarity	NPD7146	Approved
0.6222	Remote Similarity	NPD5330	Approved
0.618	Remote Similarity	NPD3668	Phase 3
0.6173	Remote Similarity	NPD4787	Phase 1
0.6146	Remote Similarity	NPD5221	Approved
0.6146	Remote Similarity	NPD7732	Phase 3
0.6146	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5222	Approved
0.6139	Remote Similarity	NPD6675	Approved
0.6139	Remote Similarity	NPD5739	Approved
0.6139	Remote Similarity	NPD7128	Approved
0.6139	Remote Similarity	NPD6402	Approved
0.6129	Remote Similarity	NPD5692	Phase 3
0.6117	Remote Similarity	NPD6372	Approved
0.6117	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD6903	Approved
0.6082	Remote Similarity	NPD4755	Approved
0.6082	Remote Similarity	NPD5173	Approved
0.6078	Remote Similarity	NPD5697	Approved
0.6078	Remote Similarity	NPD5701	Approved
0.6076	Remote Similarity	NPD375	Phase 2
0.6064	Remote Similarity	NPD5694	Approved
0.6064	Remote Similarity	NPD6050	Approved
0.6056	Remote Similarity	NPD3186	Phase 1
0.6044	Remote Similarity	NPD4623	Approved
0.6044	Remote Similarity	NPD5279	Phase 3
0.6044	Remote Similarity	NPD4519	Discontinued
0.6042	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.604	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7320	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD5091	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6649	Approved
0.598	Remote Similarity	NPD6920	Discontinued
0.5978	Remote Similarity	NPD3573	Approved
0.5977	Remote Similarity	NPD4195	Approved
0.5976	Remote Similarity	NPD4747	Approved
0.5962	Remote Similarity	NPD6013	Approved
0.5962	Remote Similarity	NPD6014	Approved
0.5962	Remote Similarity	NPD6012	Approved
0.596	Remote Similarity	NPD4700	Approved
0.596	Remote Similarity	NPD5285	Approved
0.596	Remote Similarity	NPD5286	Approved
0.596	Remote Similarity	NPD4696	Approved
0.5957	Remote Similarity	NPD5207	Approved
0.5938	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6001	Approved
0.5938	Remote Similarity	NPD7900	Approved
0.5909	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6883	Approved
0.5905	Remote Similarity	NPD7290	Approved
0.5905	Remote Similarity	NPD7102	Approved
0.59	Remote Similarity	NPD5223	Approved
0.5876	Remote Similarity	NPD5654	Approved
0.5862	Remote Similarity	NPD4802	Phase 2
0.5862	Remote Similarity	NPD4238	Approved
0.5862	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7638	Approved
0.5854	Remote Similarity	NPD4137	Phase 3
0.5849	Remote Similarity	NPD6617	Approved
0.5849	Remote Similarity	NPD6847	Approved
0.5849	Remote Similarity	NPD6869	Approved
0.5849	Remote Similarity	NPD8130	Phase 1
0.5849	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5226	Approved
0.5842	Remote Similarity	NPD4633	Approved
0.5842	Remote Similarity	NPD5211	Phase 2
0.5842	Remote Similarity	NPD5225	Approved
0.5842	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD5133	Approved
0.58	Remote Similarity	NPD7640	Approved
0.58	Remote Similarity	NPD7639	Approved
0.5797	Remote Similarity	NPD344	Approved
0.5797	Remote Similarity	NPD343	Approved
0.5797	Remote Similarity	NPD345	Approved
0.5794	Remote Similarity	NPD6882	Approved
0.5794	Remote Similarity	NPD8297	Approved
0.5789	Remote Similarity	NPD4096	Approved
0.5784	Remote Similarity	NPD5175	Approved
0.5784	Remote Similarity	NPD5174	Approved
0.5784	Remote Similarity	NPD4754	Approved
0.5783	Remote Similarity	NPD4691	Approved
0.5778	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6614	Approved
0.5758	Remote Similarity	NPD5959	Approved
0.5741	Remote Similarity	NPD4632	Approved
0.5741	Remote Similarity	NPD8298	Phase 2
0.5732	Remote Similarity	NPD6705	Phase 1
0.5732	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.573	Remote Similarity	NPD7525	Registered
0.573	Remote Similarity	NPD6928	Phase 2
0.5728	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD4243	Approved
0.5714	Remote Similarity	NPD3669	Approved
0.5714	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2266	Phase 2
0.5694	Remote Similarity	NPD9638	Phase 2
0.5686	Remote Similarity	NPD7632	Discontinued
0.5673	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD4768	Approved
0.5673	Remote Similarity	NPD6008	Approved
0.5667	Remote Similarity	NPD1780	Approved
0.5667	Remote Similarity	NPD1779	Approved
0.5663	Remote Similarity	NPD3726	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