NPASS Compound

Structure

NPC469941 OpenBabel07101718192D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 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 -0.6397 -1.0707 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 -1.8653 0.3880 0.0000 C 0 0 0 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 -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 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 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 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 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 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 5 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 10 13 1 0 0 0 0 10 20 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 4 1 6 0 0 0 13 14 1 0 0 0 0 14 17 1 1 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 20 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	343.985
LogP:	3.367
LogD:	3.07
LogS:	-3.432
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	5.614
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.363
MDCK Permeability:	1.247092404810246e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	92.35680389404297%
Volume Distribution (VD):	0.699
Pgp-substrate:	5.26904821395874%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.337
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	4.35
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.209
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.205
Skin Sensitization:	0.925
Carcinogencity:	0.208
Eye Corrosion:	0.23
Eye Irritation:	0.644
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC469941

Natural Product ID:	NPC469941
*Common Name:**	LKXILSFITASWCO-BGMRAPHESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LKXILSFITASWCO-BGMRAPHESA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-18(12-21)7-3-8-19(2)15(18)6-9-20-10-13(4-5-16(19)20)14(11-20)17(22)23/h13-16,21H,3-12H2,1-2H3,(H,22,23)/t13-,14-,15+,16-,18-,19+,20+/m0/s1
SMILES:	OC[C@]1(C)CCC[C@@]2([C@@H]1CC[C@]13[C@H]2CC[C@@H](C3)[C@H](C1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288269
PubChem CID:	52944942
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
NPO6876	Ixora coccinea	Species	Rubiaceae	Eukaryota	aerial parts	collected on the campus of Kaohsiung Medical University, Taiwan	2007-Oct	PMID[21106454]
NPO6876	Ixora coccinea	Species	Rubiaceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	31.77	%	PMID[544266]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	15.57	%	PMID[544266]

☑ 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 NPC469941 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	283
0.1-0.2	3342
0.2-0.3	16270
0.3-0.4	8323
0.4-0.5	5836
0.5-0.6	5328
0.6-0.7	2591
0.7-0.8	570
0.8-0.85	70
0.85-0.9	53
0.9-0.95	21
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476734
1.0	High Similarity	NPC319671
1.0	High Similarity	NPC252032
0.9846	High Similarity	NPC477929
0.9545	High Similarity	NPC477850
0.9531	High Similarity	NPC42060
0.9412	High Similarity	NPC167702
0.9412	High Similarity	NPC280026
0.9412	High Similarity	NPC477930
0.9403	High Similarity	NPC469940
0.9394	High Similarity	NPC64466
0.9275	High Similarity	NPC212733
0.9231	High Similarity	NPC477931
0.9231	High Similarity	NPC268736
0.9143	High Similarity	NPC4209
0.9143	High Similarity	NPC477933
0.9143	High Similarity	NPC477932
0.9091	High Similarity	NPC474221
0.9091	High Similarity	NPC478180
0.9091	High Similarity	NPC130459
0.9014	High Similarity	NPC207010
0.9014	High Similarity	NPC180199
0.9014	High Similarity	NPC143133
0.9014	High Similarity	NPC477919
0.9014	High Similarity	NPC317913
0.9014	High Similarity	NPC298168
0.9	High Similarity	NPC472311
0.9	High Similarity	NPC477934
0.8971	High Similarity	NPC108131
0.8889	High Similarity	NPC171426
0.8889	High Similarity	NPC224802
0.8889	High Similarity	NPC34046
0.8889	High Similarity	NPC324700
0.8889	High Similarity	NPC199965
0.8889	High Similarity	NPC80089
0.8889	High Similarity	NPC185465
0.8889	High Similarity	NPC476732
0.8841	High Similarity	NPC320549
0.8841	High Similarity	NPC156277
0.8841	High Similarity	NPC151018
0.8841	High Similarity	NPC58057
0.8824	High Similarity	NPC474962
0.8824	High Similarity	NPC196197
0.8767	High Similarity	NPC201276
0.8767	High Similarity	NPC80891
0.8767	High Similarity	NPC320144
0.875	High Similarity	NPC477918
0.8714	High Similarity	NPC232112
0.8714	High Similarity	NPC310766
0.863	High Similarity	NPC329117
0.8592	High Similarity	NPC472854
0.8592	High Similarity	NPC254340
0.8571	High Similarity	NPC473267
0.8551	High Similarity	NPC324607
0.8551	High Similarity	NPC131892
0.8551	High Similarity	NPC213178
0.8551	High Similarity	NPC327728
0.8551	High Similarity	NPC321732
0.8551	High Similarity	NPC6120
0.8533	High Similarity	NPC58631
0.8533	High Similarity	NPC12933
0.8493	Intermediate Similarity	NPC474404
0.8472	Intermediate Similarity	NPC174964
0.8472	Intermediate Similarity	NPC27349
0.8472	Intermediate Similarity	NPC125767
0.8472	Intermediate Similarity	NPC195155
0.8472	Intermediate Similarity	NPC273366
0.8472	Intermediate Similarity	NPC21220
0.8472	Intermediate Similarity	NPC97534
0.8472	Intermediate Similarity	NPC24014
0.8438	Intermediate Similarity	NPC476735
0.8429	Intermediate Similarity	NPC476731
0.8421	Intermediate Similarity	NPC121121
0.8421	Intermediate Similarity	NPC477935
0.8421	Intermediate Similarity	NPC61107
0.8421	Intermediate Similarity	NPC30583
0.8421	Intermediate Similarity	NPC289486
0.8406	Intermediate Similarity	NPC473225
0.84	Intermediate Similarity	NPC261616
0.84	Intermediate Similarity	NPC477851
0.84	Intermediate Similarity	NPC472853
0.8356	Intermediate Similarity	NPC475742
0.8356	Intermediate Similarity	NPC472487
0.8356	Intermediate Similarity	NPC246445
0.8356	Intermediate Similarity	NPC472486
0.8356	Intermediate Similarity	NPC5767
0.8312	Intermediate Similarity	NPC245866
0.831	Intermediate Similarity	NPC472309
0.831	Intermediate Similarity	NPC89310
0.8267	Intermediate Similarity	NPC472310
0.8243	Intermediate Similarity	NPC66105
0.8243	Intermediate Similarity	NPC475031
0.8243	Intermediate Similarity	NPC68828
0.8243	Intermediate Similarity	NPC221420
0.8243	Intermediate Similarity	NPC264602
0.8243	Intermediate Similarity	NPC23884
0.8219	Intermediate Similarity	NPC179858
0.8205	Intermediate Similarity	NPC473336
0.8205	Intermediate Similarity	NPC471044
0.8194	Intermediate Similarity	NPC161187
0.8194	Intermediate Similarity	NPC330659
0.8194	Intermediate Similarity	NPC244708
0.8182	Intermediate Similarity	NPC477936
0.8143	Intermediate Similarity	NPC180777
0.8143	Intermediate Similarity	NPC31187
0.8143	Intermediate Similarity	NPC260319
0.8143	Intermediate Similarity	NPC103647
0.8143	Intermediate Similarity	NPC474954
0.8143	Intermediate Similarity	NPC100917
0.8143	Intermediate Similarity	NPC2568
0.8143	Intermediate Similarity	NPC281203
0.8143	Intermediate Similarity	NPC469724
0.8101	Intermediate Similarity	NPC294438
0.8101	Intermediate Similarity	NPC201655
0.8101	Intermediate Similarity	NPC264317
0.8082	Intermediate Similarity	NPC133922
0.8077	Intermediate Similarity	NPC259173
0.8056	Intermediate Similarity	NPC197701
0.8056	Intermediate Similarity	NPC478227
0.8026	Intermediate Similarity	NPC52951
0.8026	Intermediate Similarity	NPC192744
0.8026	Intermediate Similarity	NPC201459
0.8	Intermediate Similarity	NPC92139
0.8	Intermediate Similarity	NPC70661
0.8	Intermediate Similarity	NPC2783
0.8	Intermediate Similarity	NPC80590
0.8	Intermediate Similarity	NPC302111
0.8	Intermediate Similarity	NPC12774
0.8	Intermediate Similarity	NPC472272
0.8	Intermediate Similarity	NPC41542
0.7975	Intermediate Similarity	NPC263974
0.7975	Intermediate Similarity	NPC319909
0.7973	Intermediate Similarity	NPC159789
0.7971	Intermediate Similarity	NPC230047
0.7971	Intermediate Similarity	NPC19311
0.7949	Intermediate Similarity	NPC170985
0.7949	Intermediate Similarity	NPC100366
0.7949	Intermediate Similarity	NPC164289
0.7949	Intermediate Similarity	NPC242771
0.7949	Intermediate Similarity	NPC311642
0.7945	Intermediate Similarity	NPC279241
0.7941	Intermediate Similarity	NPC114891
0.7922	Intermediate Similarity	NPC470609
0.7917	Intermediate Similarity	NPC91369
0.7901	Intermediate Similarity	NPC134197
0.7901	Intermediate Similarity	NPC252714
0.7901	Intermediate Similarity	NPC264005
0.7901	Intermediate Similarity	NPC33768
0.7901	Intermediate Similarity	NPC269360
0.7895	Intermediate Similarity	NPC472608
0.7895	Intermediate Similarity	NPC26029
0.7887	Intermediate Similarity	NPC470956
0.7867	Intermediate Similarity	NPC471046
0.7848	Intermediate Similarity	NPC471037
0.7821	Intermediate Similarity	NPC474484
0.7821	Intermediate Similarity	NPC48756
0.7821	Intermediate Similarity	NPC103754
0.7821	Intermediate Similarity	NPC469745
0.7821	Intermediate Similarity	NPC280781
0.7808	Intermediate Similarity	NPC290058
0.7805	Intermediate Similarity	NPC474719
0.7805	Intermediate Similarity	NPC211162
0.7805	Intermediate Similarity	NPC146937
0.7805	Intermediate Similarity	NPC16377
0.7805	Intermediate Similarity	NPC471900
0.7805	Intermediate Similarity	NPC183374
0.7794	Intermediate Similarity	NPC71460
0.7794	Intermediate Similarity	NPC218585
0.7794	Intermediate Similarity	NPC148174
0.7794	Intermediate Similarity	NPC306750
0.7792	Intermediate Similarity	NPC245029
0.7792	Intermediate Similarity	NPC31302
0.7778	Intermediate Similarity	NPC155011
0.7778	Intermediate Similarity	NPC295788
0.7778	Intermediate Similarity	NPC178541
0.7763	Intermediate Similarity	NPC212661
0.7763	Intermediate Similarity	NPC106078
0.7763	Intermediate Similarity	NPC471035
0.7763	Intermediate Similarity	NPC171658
0.775	Intermediate Similarity	NPC476038
0.775	Intermediate Similarity	NPC194937
0.7733	Intermediate Similarity	NPC132064
0.7722	Intermediate Similarity	NPC145143
0.7722	Intermediate Similarity	NPC477858
0.7722	Intermediate Similarity	NPC328007
0.7722	Intermediate Similarity	NPC148740
0.7722	Intermediate Similarity	NPC317066
0.7722	Intermediate Similarity	NPC268040
0.7722	Intermediate Similarity	NPC102156
0.7714	Intermediate Similarity	NPC243469
0.7714	Intermediate Similarity	NPC475943
0.7714	Intermediate Similarity	NPC469791
0.7714	Intermediate Similarity	NPC190827
0.7711	Intermediate Similarity	NPC24705
0.7711	Intermediate Similarity	NPC56962
0.7711	Intermediate Similarity	NPC57954
0.7711	Intermediate Similarity	NPC24772
0.7711	Intermediate Similarity	NPC213832
0.7711	Intermediate Similarity	NPC220498
0.7711	Intermediate Similarity	NPC116146

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 NPC469941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	3450
0.2-0.3	3706
0.3-0.4	977
0.4-0.5	282
0.5-0.6	235
0.6-0.7	130
0.7-0.8	9
0.8-0.85	6
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD6113	Clinical (unspecified phase)
0.9143	High Similarity	NPD6117	Approved
0.9014	High Similarity	NPD6116	Phase 1
0.8971	High Similarity	NPD4789	Approved
0.8939	High Similarity	NPD4224	Phase 2
0.8889	High Similarity	NPD6697	Approved
0.8889	High Similarity	NPD6114	Approved
0.8889	High Similarity	NPD6115	Approved
0.8889	High Similarity	NPD6118	Approved
0.8841	High Similarity	NPD6081	Approved
0.8841	High Similarity	NPD4808	Clinical (unspecified phase)
0.8841	High Similarity	NPD4809	Clinical (unspecified phase)
0.8788	High Similarity	NPD3171	Clinical (unspecified phase)
0.8696	High Similarity	NPD4244	Approved
0.8696	High Similarity	NPD4245	Approved
0.8551	High Similarity	NPD3698	Phase 2
0.8551	High Similarity	NPD3699	Clinical (unspecified phase)
0.8551	High Similarity	NPD3700	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD3702	Approved
0.8406	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD5360	Phase 3
0.831	Intermediate Similarity	NPD5777	Approved
0.8101	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3703	Phase 2
0.7808	Intermediate Similarity	NPD4758	Discontinued
0.7662	Intermediate Similarity	NPD3671	Phase 1
0.7625	Intermediate Similarity	NPD4788	Approved
0.75	Intermediate Similarity	NPD3198	Approved
0.7436	Intermediate Similarity	NPD5364	Discontinued
0.7326	Intermediate Similarity	NPD8034	Phase 2
0.7326	Intermediate Similarity	NPD8035	Phase 2
0.7317	Intermediate Similarity	NPD4786	Approved
0.7297	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4787	Phase 1
0.7073	Intermediate Similarity	NPD3667	Approved
0.7045	Intermediate Similarity	NPD6399	Phase 3
0.7015	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8418	Phase 2
0.6933	Remote Similarity	NPD6705	Phase 1
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6083	Phase 2
0.6905	Remote Similarity	NPD3666	Approved
0.6905	Remote Similarity	NPD3133	Approved
0.6905	Remote Similarity	NPD3665	Phase 1
0.6897	Remote Similarity	NPD5328	Approved
0.679	Remote Similarity	NPD3617	Approved
0.6782	Remote Similarity	NPD5737	Approved
0.6782	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7521	Approved
0.6744	Remote Similarity	NPD3618	Phase 1
0.6744	Remote Similarity	NPD7334	Approved
0.6744	Remote Similarity	NPD6409	Approved
0.6744	Remote Similarity	NPD6684	Approved
0.6744	Remote Similarity	NPD5330	Approved
0.6744	Remote Similarity	NPD7146	Approved
0.6742	Remote Similarity	NPD7515	Phase 2
0.6742	Remote Similarity	NPD6079	Approved
0.6705	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6628	Remote Similarity	NPD5329	Approved
0.6627	Remote Similarity	NPD6928	Phase 2
0.6591	Remote Similarity	NPD6903	Approved
0.6562	Remote Similarity	NPD634	Phase 3
0.6552	Remote Similarity	NPD6098	Approved
0.6552	Remote Similarity	NPD5279	Phase 3
0.6548	Remote Similarity	NPD4692	Approved
0.6548	Remote Similarity	NPD4139	Approved
0.6522	Remote Similarity	NPD5695	Phase 3
0.6512	Remote Similarity	NPD4197	Approved
0.6489	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD5696	Approved
0.6484	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD3186	Phase 1
0.6447	Remote Similarity	NPD375	Phase 2
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6429	Remote Similarity	NPD7525	Registered
0.6421	Remote Similarity	NPD7640	Approved
0.6421	Remote Similarity	NPD7639	Approved
0.642	Remote Similarity	NPD6942	Approved
0.642	Remote Similarity	NPD7339	Approved
0.6413	Remote Similarity	NPD7748	Approved
0.641	Remote Similarity	NPD3725	Approved
0.641	Remote Similarity	NPD3726	Approved
0.64	Remote Similarity	NPD7909	Approved
0.6386	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5281	Approved
0.6374	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD4690	Approved
0.6364	Remote Similarity	NPD4693	Phase 3
0.6364	Remote Similarity	NPD5205	Approved
0.6364	Remote Similarity	NPD4689	Approved
0.6364	Remote Similarity	NPD4138	Approved
0.6364	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD4629	Approved
0.6344	Remote Similarity	NPD5210	Approved
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.6333	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3668	Phase 3
0.63	Remote Similarity	NPD6881	Approved
0.63	Remote Similarity	NPD6899	Approved
0.63	Remote Similarity	NPD7320	Approved
0.6289	Remote Similarity	NPD7632	Discontinued
0.6277	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4697	Phase 3
0.6277	Remote Similarity	NPD5221	Approved
0.6277	Remote Similarity	NPD5222	Approved
0.6238	Remote Similarity	NPD6373	Approved
0.6238	Remote Similarity	NPD6372	Approved
0.6222	Remote Similarity	NPD5208	Approved
0.6211	Remote Similarity	NPD5173	Approved
0.6211	Remote Similarity	NPD4755	Approved
0.6211	Remote Similarity	NPD7902	Approved
0.62	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD4238	Approved
0.619	Remote Similarity	NPD4802	Phase 2
0.618	Remote Similarity	NPD5690	Phase 2
0.618	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4694	Approved
0.618	Remote Similarity	NPD5280	Approved
0.6176	Remote Similarity	NPD7290	Approved
0.6176	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD6883	Approved
0.617	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8298	Phase 2
0.6145	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6011	Approved
0.6119	Remote Similarity	NPD2266	Phase 2
0.6117	Remote Similarity	NPD6847	Approved
0.6117	Remote Similarity	NPD6649	Approved
0.6117	Remote Similarity	NPD6869	Approved
0.6117	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6650	Approved
0.6117	Remote Similarity	NPD8130	Phase 1
0.61	Remote Similarity	NPD6920	Discontinued
0.6098	Remote Similarity	NPD6924	Approved
0.6098	Remote Similarity	NPD6926	Approved
0.6094	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4696	Approved
0.6082	Remote Similarity	NPD5285	Approved
0.6082	Remote Similarity	NPD6404	Discontinued
0.6082	Remote Similarity	NPD5286	Approved
0.6082	Remote Similarity	NPD4700	Approved
0.6078	Remote Similarity	NPD6013	Approved
0.6078	Remote Similarity	NPD6014	Approved
0.6078	Remote Similarity	NPD6012	Approved
0.6058	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD8297	Approved
0.6049	Remote Similarity	NPD4243	Approved
0.6038	Remote Similarity	NPD6940	Discontinued
0.6022	Remote Similarity	NPD6050	Approved
0.6022	Remote Similarity	NPD5693	Phase 1
0.602	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD4776	Phase 2
0.6	Remote Similarity	NPD4777	Suspended
0.598	Remote Similarity	NPD6415	Discontinued
0.596	Remote Similarity	NPD5225	Approved
0.596	Remote Similarity	NPD5211	Phase 2
0.596	Remote Similarity	NPD5226	Approved
0.596	Remote Similarity	NPD4633	Approved
0.596	Remote Similarity	NPD5224	Approved
0.5952	Remote Similarity	NPD6933	Approved
0.5938	Remote Similarity	NPD2270	Approved
0.5938	Remote Similarity	NPD7614	Phase 1
0.593	Remote Similarity	NPD4195	Approved
0.5926	Remote Similarity	NPD4747	Approved
0.5914	Remote Similarity	NPD5207	Approved
0.5914	Remote Similarity	NPD5692	Phase 3
0.5904	Remote Similarity	NPD4784	Approved
0.5904	Remote Similarity	NPD4785	Approved
0.59	Remote Similarity	NPD5175	Approved
0.59	Remote Similarity	NPD5174	Approved
0.59	Remote Similarity	NPD4754	Approved
0.5895	Remote Similarity	NPD7900	Approved
0.5895	Remote Similarity	NPD6001	Approved
0.5895	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6868	Approved
0.5882	Remote Similarity	NPD6412	Phase 2
0.5862	Remote Similarity	NPD4695	Discontinued
0.5862	Remote Similarity	NPD4748	Discontinued
0.5862	Remote Similarity	NPD5368	Approved
0.5851	Remote Similarity	NPD5694	Approved
0.5851	Remote Similarity	NPD7637	Suspended
0.5851	Remote Similarity	NPD6411	Approved
0.5849	Remote Similarity	NPD4632	Approved
0.5843	Remote Similarity	NPD5362	Discontinued
0.5842	Remote Similarity	NPD5141	Approved
0.5833	Remote Similarity	NPD2257	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