NPASS Compound

Structure

NPC472486 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 1 1 1 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 9 1 1 0 0 0 13 16 1 0 0 0 0 13 21 1 6 0 0 0 14 18 1 0 0 0 0 14 19 1 1 0 0 0 15 18 1 0 0 0 0 15 22 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 19 4 1 1 0 0 0 20 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	343.985
LogP:	2.662
LogD:	3.207
LogS:	-3.78
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	5.771
Fsp3:	0.95
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:	-4.724
MDCK Permeability:	1.9028106180485338e-05
Pgp-inhibitor:	0.732
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797
Plasma Protein Binding (PPB):	65.57459259033203%
Volume Distribution (VD):	0.994
Pgp-substrate:	30.885082244873047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.29
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.375
CYP3A4-inhibitor:	0.547
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	9.923
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.415
Carcinogencity:	0.215
Eye Corrosion:	0.863
Eye Irritation:	0.83
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC472486

Natural Product ID:	NPC472486
*Common Name:**	ITXNSRHFHSYGII-YDNJNAECSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ITXNSRHFHSYGII-YDNJNAECSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-11-12-9-13(21)16-19(4)7-6-15(22)18(2,3)14(19)5-8-20(16,10-12)17(11)23/h11-16,21-22H,5-10H2,1-4H3/t11-,12-,13+,14-,15-,16+,19-,20-/m1/s1
SMILES:	CC1C2CC(C3C4(CCC(C(C4CCC3(C2)C1=O)(C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426494
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ 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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[491668]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[491668]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[491668]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[491668]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[491668]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[491668]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[491668]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[491668]

☑ 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 NPC472486 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	319
0.1-0.2	3163
0.2-0.3	12315
0.3-0.4	12328
0.4-0.5	5637
0.5-0.6	4961
0.6-0.7	2861
0.7-0.8	930
0.8-0.85	106
0.85-0.9	39
0.9-0.95	32
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472487
0.9857	High Similarity	NPC21220
0.9857	High Similarity	NPC125767
0.9583	High Similarity	NPC221420
0.9571	High Similarity	NPC232112
0.9444	High Similarity	NPC475742
0.9444	High Similarity	NPC5767
0.9429	High Similarity	NPC320549
0.9429	High Similarity	NPC156277
0.9429	High Similarity	NPC151018
0.9429	High Similarity	NPC58057
0.9429	High Similarity	NPC89310
0.9324	High Similarity	NPC320144
0.9315	High Similarity	NPC23884
0.9306	High Similarity	NPC97534
0.9306	High Similarity	NPC195155
0.9306	High Similarity	NPC174964
0.9306	High Similarity	NPC159789
0.9306	High Similarity	NPC273366
0.9189	High Similarity	NPC185465
0.9167	High Similarity	NPC133922
0.9167	High Similarity	NPC254340
0.9143	High Similarity	NPC327728
0.9143	High Similarity	NPC213178
0.9143	High Similarity	NPC6120
0.9143	High Similarity	NPC131892
0.9054	High Similarity	NPC475031
0.9041	High Similarity	NPC212733
0.8961	High Similarity	NPC317066
0.8919	High Similarity	NPC4209
0.8904	High Similarity	NPC280026
0.8904	High Similarity	NPC167702
0.8857	High Similarity	NPC472984
0.8846	High Similarity	NPC327451
0.88	High Similarity	NPC143133
0.88	High Similarity	NPC298168
0.88	High Similarity	NPC317913
0.88	High Similarity	NPC207010
0.8767	High Similarity	NPC310766
0.8734	High Similarity	NPC50438
0.8718	High Similarity	NPC289486
0.8718	High Similarity	NPC268040
0.8718	High Similarity	NPC30583
0.8718	High Similarity	NPC61107
0.8701	High Similarity	NPC470609
0.8701	High Similarity	NPC477851
0.8684	High Similarity	NPC224802
0.8684	High Similarity	NPC34046
0.8684	High Similarity	NPC80089
0.8684	High Similarity	NPC171426
0.8684	High Similarity	NPC324700
0.8649	High Similarity	NPC168511
0.8649	High Similarity	NPC159325
0.8611	High Similarity	NPC324607
0.8611	High Similarity	NPC321732
0.859	High Similarity	NPC58631
0.859	High Similarity	NPC469745
0.8571	High Similarity	NPC201276
0.8571	High Similarity	NPC80891
0.8519	High Similarity	NPC476727
0.8519	High Similarity	NPC80700
0.8519	High Similarity	NPC476726
0.8514	High Similarity	NPC282905
0.8514	High Similarity	NPC477229
0.8514	High Similarity	NPC68426
0.85	High Similarity	NPC474482
0.85	High Similarity	NPC146683
0.85	High Similarity	NPC475745
0.8481	Intermediate Similarity	NPC328007
0.8472	Intermediate Similarity	NPC474954
0.8462	Intermediate Similarity	NPC164999
0.8434	Intermediate Similarity	NPC61688
0.8421	Intermediate Similarity	NPC108840
0.8421	Intermediate Similarity	NPC471046
0.8415	Intermediate Similarity	NPC263802
0.8415	Intermediate Similarity	NPC4643
0.8415	Intermediate Similarity	NPC57469
0.84	Intermediate Similarity	NPC472854
0.8378	Intermediate Similarity	NPC473267
0.8375	Intermediate Similarity	NPC118800
0.8375	Intermediate Similarity	NPC475726
0.8375	Intermediate Similarity	NPC472743
0.8356	Intermediate Similarity	NPC252032
0.8356	Intermediate Similarity	NPC476734
0.8356	Intermediate Similarity	NPC469941
0.8356	Intermediate Similarity	NPC319671
0.8354	Intermediate Similarity	NPC12933
0.8333	Intermediate Similarity	NPC476296
0.8333	Intermediate Similarity	NPC472310
0.8312	Intermediate Similarity	NPC264602
0.8293	Intermediate Similarity	NPC472272
0.8293	Intermediate Similarity	NPC302111
0.8293	Intermediate Similarity	NPC472738
0.8289	Intermediate Similarity	NPC472311
0.8289	Intermediate Similarity	NPC267753
0.8286	Intermediate Similarity	NPC114891
0.8272	Intermediate Similarity	NPC471044
0.8272	Intermediate Similarity	NPC473336
0.8272	Intermediate Similarity	NPC474996
0.8267	Intermediate Similarity	NPC81759
0.825	Intermediate Similarity	NPC121121
0.8243	Intermediate Similarity	NPC477929
0.8243	Intermediate Similarity	NPC476731
0.8228	Intermediate Similarity	NPC261616
0.8219	Intermediate Similarity	NPC473225
0.8205	Intermediate Similarity	NPC329117
0.8194	Intermediate Similarity	NPC142712
0.8193	Intermediate Similarity	NPC472497
0.8193	Intermediate Similarity	NPC174619
0.8193	Intermediate Similarity	NPC153604
0.8193	Intermediate Similarity	NPC472495
0.8171	Intermediate Similarity	NPC76518
0.8171	Intermediate Similarity	NPC292553
0.8158	Intermediate Similarity	NPC130011
0.8143	Intermediate Similarity	NPC148174
0.8143	Intermediate Similarity	NPC71460
0.8143	Intermediate Similarity	NPC218585
0.814	Intermediate Similarity	NPC476189
0.814	Intermediate Similarity	NPC224060
0.814	Intermediate Similarity	NPC244356
0.8133	Intermediate Similarity	NPC126642
0.8125	Intermediate Similarity	NPC50658
0.8108	Intermediate Similarity	NPC196197
0.8095	Intermediate Similarity	NPC90676
0.8095	Intermediate Similarity	NPC477614
0.8095	Intermediate Similarity	NPC474719
0.8095	Intermediate Similarity	NPC226491
0.8095	Intermediate Similarity	NPC472739
0.8082	Intermediate Similarity	NPC473230
0.8082	Intermediate Similarity	NPC48079
0.8082	Intermediate Similarity	NPC475884
0.8077	Intermediate Similarity	NPC472746
0.8056	Intermediate Similarity	NPC41577
0.8056	Intermediate Similarity	NPC473276
0.8056	Intermediate Similarity	NPC474380
0.8052	Intermediate Similarity	NPC27349
0.8052	Intermediate Similarity	NPC24014
0.8049	Intermediate Similarity	NPC74595
0.8049	Intermediate Similarity	NPC264665
0.8049	Intermediate Similarity	NPC319909
0.8049	Intermediate Similarity	NPC474233
0.8023	Intermediate Similarity	NPC52756
0.8	Intermediate Similarity	NPC56962
0.8	Intermediate Similarity	NPC108131
0.8	Intermediate Similarity	NPC477850
0.8	Intermediate Similarity	NPC24705
0.7976	Intermediate Similarity	NPC202937
0.7975	Intermediate Similarity	NPC478128
0.7975	Intermediate Similarity	NPC472608
0.7973	Intermediate Similarity	NPC2568
0.7973	Intermediate Similarity	NPC103647
0.7973	Intermediate Similarity	NPC472741
0.7973	Intermediate Similarity	NPC180777
0.7973	Intermediate Similarity	NPC260319
0.7955	Intermediate Similarity	NPC287354
0.7955	Intermediate Similarity	NPC62407
0.7952	Intermediate Similarity	NPC264317
0.7952	Intermediate Similarity	NPC62572
0.7952	Intermediate Similarity	NPC294438
0.7952	Intermediate Similarity	NPC473350
0.7945	Intermediate Similarity	NPC44122
0.7945	Intermediate Similarity	NPC42060
0.7931	Intermediate Similarity	NPC294263
0.7931	Intermediate Similarity	NPC161035
0.7927	Intermediate Similarity	NPC163616
0.7927	Intermediate Similarity	NPC471036
0.7927	Intermediate Similarity	NPC472498
0.7927	Intermediate Similarity	NPC291320
0.7922	Intermediate Similarity	NPC477930
0.7917	Intermediate Similarity	NPC69149
0.7917	Intermediate Similarity	NPC281540
0.7917	Intermediate Similarity	NPC159654
0.7917	Intermediate Similarity	NPC167995
0.7917	Intermediate Similarity	NPC118937
0.7907	Intermediate Similarity	NPC80401
0.7907	Intermediate Similarity	NPC180849
0.7907	Intermediate Similarity	NPC46758
0.7907	Intermediate Similarity	NPC77756
0.7907	Intermediate Similarity	NPC100313
0.7901	Intermediate Similarity	NPC476071
0.7901	Intermediate Similarity	NPC280781
0.7901	Intermediate Similarity	NPC48756
0.7895	Intermediate Similarity	NPC469940
0.7882	Intermediate Similarity	NPC328539
0.7882	Intermediate Similarity	NPC53911
0.7882	Intermediate Similarity	NPC131470
0.7882	Intermediate Similarity	NPC193360
0.7882	Intermediate Similarity	NPC143767
0.7875	Intermediate Similarity	NPC31302
0.7875	Intermediate Similarity	NPC52951
0.7875	Intermediate Similarity	NPC201459
0.7875	Intermediate Similarity	NPC245029
0.7867	Intermediate Similarity	NPC299948
0.7867	Intermediate Similarity	NPC470830
0.7867	Intermediate Similarity	NPC66407
0.7867	Intermediate Similarity	NPC64466
0.7867	Intermediate Similarity	NPC129829
0.7867	Intermediate Similarity	NPC241085
0.7867	Intermediate Similarity	NPC107919
0.7867	Intermediate Similarity	NPC254037

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 NPC472486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	3584
0.2-0.3	3614
0.3-0.4	985
0.4-0.5	216
0.5-0.6	199
0.6-0.7	134
0.7-0.8	28
0.8-0.85	5
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9429	High Similarity	NPD4808	Clinical (unspecified phase)
0.9429	High Similarity	NPD4809	Clinical (unspecified phase)
0.9306	High Similarity	NPD3703	Phase 2
0.9143	High Similarity	NPD3699	Clinical (unspecified phase)
0.9143	High Similarity	NPD3700	Clinical (unspecified phase)
0.8919	High Similarity	NPD6117	Approved
0.8904	High Similarity	NPD6113	Clinical (unspecified phase)
0.88	High Similarity	NPD6116	Phase 1
0.875	High Similarity	NPD4244	Approved
0.875	High Similarity	NPD4245	Approved
0.875	High Similarity	NPD4789	Approved
0.8732	High Similarity	NPD5361	Clinical (unspecified phase)
0.8732	High Similarity	NPD5360	Phase 3
0.8684	High Similarity	NPD6115	Approved
0.8684	High Similarity	NPD6114	Approved
0.8684	High Similarity	NPD6697	Approved
0.8684	High Similarity	NPD6118	Approved
0.8611	High Similarity	NPD3698	Phase 2
0.8571	High Similarity	NPD3171	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3671	Phase 1
0.8133	Intermediate Similarity	NPD4758	Discontinued
0.8	Intermediate Similarity	NPD5328	Approved
0.7952	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4224	Phase 2
0.7895	Intermediate Similarity	NPD6081	Approved
0.7867	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6079	Approved
0.775	Intermediate Similarity	NPD5364	Discontinued
0.7662	Intermediate Similarity	NPD5777	Approved
0.7647	Intermediate Similarity	NPD3618	Phase 1
0.7619	Intermediate Similarity	NPD4786	Approved
0.7595	Intermediate Similarity	NPD3702	Approved
0.7532	Intermediate Similarity	NPD4787	Phase 1
0.75	Intermediate Similarity	NPD4788	Approved
0.7473	Intermediate Similarity	NPD4697	Phase 3
0.7416	Intermediate Similarity	NPD8035	Phase 2
0.7416	Intermediate Similarity	NPD8034	Phase 2
0.7381	Intermediate Similarity	NPD3667	Approved
0.7283	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5221	Approved
0.7283	Intermediate Similarity	NPD5222	Approved
0.7204	Intermediate Similarity	NPD4755	Approved
0.7204	Intermediate Similarity	NPD5173	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7053	Intermediate Similarity	NPD4700	Approved
0.7053	Intermediate Similarity	NPD5286	Approved
0.7053	Intermediate Similarity	NPD5285	Approved
0.7053	Intermediate Similarity	NPD4696	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.6979	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD6399	Phase 3
0.6941	Remote Similarity	NPD7525	Registered
0.6939	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5225	Approved
0.6907	Remote Similarity	NPD4633	Approved
0.6907	Remote Similarity	NPD5226	Approved
0.6907	Remote Similarity	NPD5211	Phase 2
0.6907	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD8418	Phase 2
0.6869	Remote Similarity	NPD7128	Approved
0.6869	Remote Similarity	NPD5739	Approved
0.6869	Remote Similarity	NPD6402	Approved
0.6869	Remote Similarity	NPD6675	Approved
0.6848	Remote Similarity	NPD7515	Phase 2
0.6837	Remote Similarity	NPD5175	Approved
0.6837	Remote Similarity	NPD5174	Approved
0.6837	Remote Similarity	NPD4754	Approved
0.6832	Remote Similarity	NPD6372	Approved
0.6832	Remote Similarity	NPD6373	Approved
0.6768	Remote Similarity	NPD5141	Approved
0.6744	Remote Similarity	NPD6928	Phase 2
0.6733	Remote Similarity	NPD6881	Approved
0.6733	Remote Similarity	NPD7320	Approved
0.6733	Remote Similarity	NPD6899	Approved
0.6706	Remote Similarity	NPD3617	Approved
0.67	Remote Similarity	NPD4768	Approved
0.67	Remote Similarity	NPD4767	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3198	Approved
0.6634	Remote Similarity	NPD5701	Approved
0.6634	Remote Similarity	NPD5697	Approved
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD3668	Phase 3
0.6602	Remote Similarity	NPD7290	Approved
0.6602	Remote Similarity	NPD7102	Approved
0.6602	Remote Similarity	NPD6883	Approved
0.6591	Remote Similarity	NPD4221	Approved
0.6591	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD6011	Approved
0.6569	Remote Similarity	NPD5168	Approved
0.6569	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD4730	Approved
0.6569	Remote Similarity	NPD5128	Approved
0.6556	Remote Similarity	NPD5329	Approved
0.6548	Remote Similarity	NPD6942	Approved
0.6548	Remote Similarity	NPD7339	Approved
0.6538	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6617	Approved
0.6538	Remote Similarity	NPD8130	Phase 1
0.6538	Remote Similarity	NPD6847	Approved
0.6538	Remote Similarity	NPD6869	Approved
0.6535	Remote Similarity	NPD6920	Discontinued
0.6526	Remote Similarity	NPD7748	Approved
0.6505	Remote Similarity	NPD6013	Approved
0.6505	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD6012	Approved
0.6495	Remote Similarity	NPD7902	Approved
0.6477	Remote Similarity	NPD4139	Approved
0.6477	Remote Similarity	NPD4692	Approved
0.6476	Remote Similarity	NPD6882	Approved
0.6476	Remote Similarity	NPD8297	Approved
0.6458	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6444	Remote Similarity	NPD4197	Approved
0.6442	Remote Similarity	NPD5135	Approved
0.6442	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD5249	Phase 3
0.6442	Remote Similarity	NPD5251	Approved
0.6442	Remote Similarity	NPD5250	Approved
0.6442	Remote Similarity	NPD5247	Approved
0.6442	Remote Similarity	NPD5169	Approved
0.6442	Remote Similarity	NPD5248	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.642	Remote Similarity	NPD6705	Phase 1
0.6408	Remote Similarity	NPD6415	Discontinued
0.6381	Remote Similarity	NPD5215	Approved
0.6381	Remote Similarity	NPD5127	Approved
0.6381	Remote Similarity	NPD5217	Approved
0.6381	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6084	Phase 2
0.6327	Remote Similarity	NPD6083	Phase 2
0.6304	Remote Similarity	NPD4689	Approved
0.6304	Remote Similarity	NPD4693	Phase 3
0.6304	Remote Similarity	NPD4138	Approved
0.6304	Remote Similarity	NPD4688	Approved
0.6304	Remote Similarity	NPD4690	Approved
0.6304	Remote Similarity	NPD7521	Approved
0.6304	Remote Similarity	NPD7334	Approved
0.6304	Remote Similarity	NPD5205	Approved
0.6304	Remote Similarity	NPD7146	Approved
0.6304	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD5330	Approved
0.6304	Remote Similarity	NPD6409	Approved
0.6296	Remote Similarity	NPD6868	Approved
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4632	Approved
0.6262	Remote Similarity	NPD8298	Phase 2
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7632	Discontinued
0.6216	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6700	Approved
0.6204	Remote Similarity	NPD5167	Approved
0.6186	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7900	Approved
0.6182	Remote Similarity	NPD6335	Approved
0.618	Remote Similarity	NPD4748	Discontinued
0.617	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD6672	Approved
0.617	Remote Similarity	NPD5737	Approved
0.6147	Remote Similarity	NPD6274	Approved
0.6146	Remote Similarity	NPD6703	Approved
0.6146	Remote Similarity	NPD6702	Approved
0.6143	Remote Similarity	NPD385	Approved
0.6143	Remote Similarity	NPD384	Approved
0.6139	Remote Similarity	NPD1700	Approved
0.6129	Remote Similarity	NPD4694	Approved
0.6129	Remote Similarity	NPD5690	Phase 2
0.6129	Remote Similarity	NPD5280	Approved
0.6126	Remote Similarity	NPD7100	Approved
0.6126	Remote Similarity	NPD7101	Approved
0.6122	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5696	Approved
0.6091	Remote Similarity	NPD7115	Discovery
0.6091	Remote Similarity	NPD6009	Approved
0.6091	Remote Similarity	NPD6317	Approved
0.6071	Remote Similarity	NPD6059	Approved
0.6071	Remote Similarity	NPD6054	Approved
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.6036	Remote Similarity	NPD6314	Approved
0.6036	Remote Similarity	NPD6313	Approved
0.6018	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6908	Approved
0.6018	Remote Similarity	NPD6909	Approved
0.5979	Remote Similarity	NPD5281	Approved
0.5979	Remote Similarity	NPD5284	Approved
0.5965	Remote Similarity	NPD6370	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