NPASS Compound

Structure

NPC469691 OpenBabel07101718332D 22 24 0 0 1 0 0 0 0 0999 V2000 3.8501 -0.1928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3057 -0.9966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3121 -4.3055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9247 -2.4217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7474 -0.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3486 -2.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4399 -1.8133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1520 -3.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5723 -1.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0849 -3.6112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7903 -0.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -3.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3458 -1.0149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2448 -3.5235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9291 -1.9738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2888 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8817 -1.8553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7474 -2.9164 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2315 -2.9064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.648
LogD:	4.152
LogS:	-5.187
# Rotatable Bonds:	0
TPSA:	29.6
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	4.895
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.636
MDCK Permeability:	1.762174542818684e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.828
30% Bioavailability (F30%):	0.423

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	94.36695098876953%
Volume Distribution (VD):	0.907
Pgp-substrate:	3.2765541076660156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.31
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.148
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.495

ADMET: Excretion

Clearance (CL):	9.719
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.355
Drug-inuced Liver Injury (DILI):	0.483
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.948
Carcinogencity:	0.684
Eye Corrosion:	0.93
Eye Irritation:	0.772
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC469691

Natural Product ID:	NPC469691
*Common Name:**	DAAUGGLPOJTNDZ-YLMLULSTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DAAUGGLPOJTNDZ-YLMLULSTSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)18-15-9-11-20(5)17(22-20)7-6-14(3)8-10-19(15,4)12-16(18)21/h8,15,17H,6-7,9-12H2,1-5H3/b14-8+/t15-,17+,19-,20+/m1/s1
SMILES:	CC1=CCC2(CC(=O)C(=C(C)C)C2CCC3(C(O3)CC1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099121
PubChem CID:	46888355
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

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	=	23200.0	nM	PMID[551794]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	<=	50.0	%	PMID[551794]

☑ 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 NPC469691 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	194
0.1-0.2	1603
0.2-0.3	8648
0.3-0.4	15124
0.4-0.5	7475
0.5-0.6	6372
0.6-0.7	2924
0.7-0.8	332
0.8-0.85	11
0.85-0.9	6
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167049
0.9571	High Similarity	NPC469678
0.9571	High Similarity	NPC475771
0.9571	High Similarity	NPC469669
0.9565	High Similarity	NPC92909
0.9565	High Similarity	NPC107783
0.9167	High Similarity	NPC226242
0.8831	High Similarity	NPC475622
0.8831	High Similarity	NPC108045
0.8667	High Similarity	NPC474056
0.8592	High Similarity	NPC477448
0.8592	High Similarity	NPC477449
0.8553	High Similarity	NPC469608
0.85	High Similarity	NPC261253
0.85	High Similarity	NPC474045
0.8481	Intermediate Similarity	NPC475796
0.8312	Intermediate Similarity	NPC469690
0.8272	Intermediate Similarity	NPC469676
0.8228	Intermediate Similarity	NPC145963
0.8194	Intermediate Similarity	NPC469688
0.8182	Intermediate Similarity	NPC207186
0.8158	Intermediate Similarity	NPC469646
0.8143	Intermediate Similarity	NPC287744
0.8143	Intermediate Similarity	NPC140233
0.8088	Intermediate Similarity	NPC259261
0.8082	Intermediate Similarity	NPC261398
0.8077	Intermediate Similarity	NPC476177
0.8077	Intermediate Similarity	NPC469620
0.7941	Intermediate Similarity	NPC94991
0.7941	Intermediate Similarity	NPC266295
0.7927	Intermediate Similarity	NPC96621
0.7927	Intermediate Similarity	NPC323765
0.7922	Intermediate Similarity	NPC215481
0.7875	Intermediate Similarity	NPC136150
0.7857	Intermediate Similarity	NPC228574
0.7857	Intermediate Similarity	NPC294304
0.7848	Intermediate Similarity	NPC229204
0.7838	Intermediate Similarity	NPC469677
0.7831	Intermediate Similarity	NPC195640
0.7821	Intermediate Similarity	NPC15975
0.7821	Intermediate Similarity	NPC195785
0.7792	Intermediate Similarity	NPC474011
0.7792	Intermediate Similarity	NPC251435
0.7792	Intermediate Similarity	NPC475861
0.7763	Intermediate Similarity	NPC470237
0.775	Intermediate Similarity	NPC304795
0.7733	Intermediate Similarity	NPC475310
0.7714	Intermediate Similarity	NPC25853
0.7703	Intermediate Similarity	NPC469679
0.7692	Intermediate Similarity	NPC271070
0.7683	Intermediate Similarity	NPC193198
0.7674	Intermediate Similarity	NPC49946
0.7674	Intermediate Similarity	NPC306168
0.7662	Intermediate Similarity	NPC469643
0.7662	Intermediate Similarity	NPC469641
0.7654	Intermediate Similarity	NPC39411
0.7654	Intermediate Similarity	NPC475665
0.7654	Intermediate Similarity	NPC255580
0.764	Intermediate Similarity	NPC477354
0.7639	Intermediate Similarity	NPC473902
0.7625	Intermediate Similarity	NPC617
0.7625	Intermediate Similarity	NPC181195
0.7625	Intermediate Similarity	NPC261125
0.7625	Intermediate Similarity	NPC80999
0.76	Intermediate Similarity	NPC144511
0.76	Intermediate Similarity	NPC22301
0.76	Intermediate Similarity	NPC296522
0.7595	Intermediate Similarity	NPC276769
0.7595	Intermediate Similarity	NPC186109
0.759	Intermediate Similarity	NPC321187
0.759	Intermediate Similarity	NPC85774
0.759	Intermediate Similarity	NPC227064
0.759	Intermediate Similarity	NPC214043
0.759	Intermediate Similarity	NPC58841
0.759	Intermediate Similarity	NPC329043
0.759	Intermediate Similarity	NPC161423
0.759	Intermediate Similarity	NPC473246
0.7586	Intermediate Similarity	NPC262870
0.7564	Intermediate Similarity	NPC216791
0.7564	Intermediate Similarity	NPC474419
0.7564	Intermediate Similarity	NPC77501
0.7564	Intermediate Similarity	NPC114236
0.7558	Intermediate Similarity	NPC170775
0.7556	Intermediate Similarity	NPC151488
0.7536	Intermediate Similarity	NPC230823
0.7536	Intermediate Similarity	NPC49575
0.7536	Intermediate Similarity	NPC267626
0.7536	Intermediate Similarity	NPC55004
0.7534	Intermediate Similarity	NPC474329
0.7534	Intermediate Similarity	NPC474304
0.7531	Intermediate Similarity	NPC45495
0.7531	Intermediate Similarity	NPC47747
0.75	Intermediate Similarity	NPC471220
0.75	Intermediate Similarity	NPC202824
0.75	Intermediate Similarity	NPC470574
0.75	Intermediate Similarity	NPC37816
0.75	Intermediate Similarity	NPC469996
0.75	Intermediate Similarity	NPC300985
0.75	Intermediate Similarity	NPC128276
0.75	Intermediate Similarity	NPC477361
0.75	Intermediate Similarity	NPC476678
0.7473	Intermediate Similarity	NPC477355
0.7471	Intermediate Similarity	NPC474842
0.7471	Intermediate Similarity	NPC475965
0.747	Intermediate Similarity	NPC470047
0.747	Intermediate Similarity	NPC53867
0.747	Intermediate Similarity	NPC470046
0.7468	Intermediate Similarity	NPC266159
0.7468	Intermediate Similarity	NPC472967
0.7442	Intermediate Similarity	NPC476707
0.7442	Intermediate Similarity	NPC476706
0.7439	Intermediate Similarity	NPC141810
0.7429	Intermediate Similarity	NPC30215
0.7416	Intermediate Similarity	NPC174051
0.7416	Intermediate Similarity	NPC67831
0.7412	Intermediate Similarity	NPC474733
0.7412	Intermediate Similarity	NPC327115
0.7412	Intermediate Similarity	NPC470051
0.7412	Intermediate Similarity	NPC145879
0.7412	Intermediate Similarity	NPC470050
0.7412	Intermediate Similarity	NPC474732
0.7412	Intermediate Similarity	NPC474778
0.7412	Intermediate Similarity	NPC31564
0.7407	Intermediate Similarity	NPC471740
0.7407	Intermediate Similarity	NPC182550
0.7407	Intermediate Similarity	NPC136033
0.7407	Intermediate Similarity	NPC7232
0.7403	Intermediate Similarity	NPC144627
0.7397	Intermediate Similarity	NPC212210
0.7391	Intermediate Similarity	NPC112167
0.7386	Intermediate Similarity	NPC221282
0.7386	Intermediate Similarity	NPC190442
0.7386	Intermediate Similarity	NPC218301
0.7381	Intermediate Similarity	NPC100391
0.7381	Intermediate Similarity	NPC238197
0.7381	Intermediate Similarity	NPC90446
0.7381	Intermediate Similarity	NPC475100
0.7381	Intermediate Similarity	NPC237712
0.7375	Intermediate Similarity	NPC476325
0.7375	Intermediate Similarity	NPC476264
0.7375	Intermediate Similarity	NPC211279
0.7375	Intermediate Similarity	NPC197659
0.7375	Intermediate Similarity	NPC472300
0.7375	Intermediate Similarity	NPC57744
0.7368	Intermediate Similarity	NPC61702
0.7368	Intermediate Similarity	NPC162867
0.7361	Intermediate Similarity	NPC97322
0.7361	Intermediate Similarity	NPC475795
0.7349	Intermediate Similarity	NPC20262
0.7349	Intermediate Similarity	NPC256750
0.7349	Intermediate Similarity	NPC328351
0.7349	Intermediate Similarity	NPC193347
0.7349	Intermediate Similarity	NPC35556
0.7349	Intermediate Similarity	NPC151519
0.7342	Intermediate Similarity	NPC113639
0.7326	Intermediate Similarity	NPC471739
0.7326	Intermediate Similarity	NPC38885
0.7326	Intermediate Similarity	NPC58063
0.7326	Intermediate Similarity	NPC136548
0.7326	Intermediate Similarity	NPC287079
0.7326	Intermediate Similarity	NPC475740
0.7326	Intermediate Similarity	NPC141292
0.7317	Intermediate Similarity	NPC69271
0.7317	Intermediate Similarity	NPC472948
0.7317	Intermediate Similarity	NPC74673
0.7317	Intermediate Similarity	NPC302426
0.7312	Intermediate Similarity	NPC477356
0.7308	Intermediate Similarity	NPC300940
0.7308	Intermediate Similarity	NPC472956
0.7303	Intermediate Similarity	NPC125180
0.7303	Intermediate Similarity	NPC229976
0.7294	Intermediate Similarity	NPC474547
0.7294	Intermediate Similarity	NPC21471
0.7294	Intermediate Similarity	NPC189311
0.7294	Intermediate Similarity	NPC78089
0.7294	Intermediate Similarity	NPC33570
0.7294	Intermediate Similarity	NPC470048
0.7294	Intermediate Similarity	NPC469948
0.7294	Intermediate Similarity	NPC161957
0.7294	Intermediate Similarity	NPC202868
0.7294	Intermediate Similarity	NPC470223
0.7284	Intermediate Similarity	NPC475994
0.7284	Intermediate Similarity	NPC478247
0.7284	Intermediate Similarity	NPC478246
0.7284	Intermediate Similarity	NPC321180
0.7284	Intermediate Similarity	NPC35574
0.7284	Intermediate Similarity	NPC253749
0.7284	Intermediate Similarity	NPC299235
0.7284	Intermediate Similarity	NPC474341
0.7283	Intermediate Similarity	NPC471582
0.7273	Intermediate Similarity	NPC472955
0.7273	Intermediate Similarity	NPC280256
0.7262	Intermediate Similarity	NPC476082
0.7262	Intermediate Similarity	NPC272814
0.7262	Intermediate Similarity	NPC278648
0.7262	Intermediate Similarity	NPC475989
0.7262	Intermediate Similarity	NPC473629
0.7262	Intermediate Similarity	NPC62214
0.7262	Intermediate Similarity	NPC215294
0.726	Intermediate Similarity	NPC32285

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 NPC469691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	2256
0.2-0.3	4275
0.3-0.4	1662
0.4-0.5	403
0.5-0.6	219
0.6-0.7	140
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7831	Intermediate Similarity	NPD7334	Approved
0.7831	Intermediate Similarity	NPD5330	Approved
0.7831	Intermediate Similarity	NPD6684	Approved
0.7831	Intermediate Similarity	NPD7521	Approved
0.7831	Intermediate Similarity	NPD6409	Approved
0.7831	Intermediate Similarity	NPD7146	Approved
0.7647	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6903	Approved
0.759	Intermediate Similarity	NPD3133	Approved
0.759	Intermediate Similarity	NPD3666	Approved
0.759	Intermediate Similarity	NPD3665	Phase 1
0.7442	Intermediate Similarity	NPD5737	Approved
0.7442	Intermediate Similarity	NPD6672	Approved
0.7412	Intermediate Similarity	NPD5279	Phase 3
0.7412	Intermediate Similarity	NPD3618	Phase 1
0.7349	Intermediate Similarity	NPD4221	Approved
0.7349	Intermediate Similarity	NPD4223	Phase 3
0.7349	Intermediate Similarity	NPD3667	Approved
0.7241	Intermediate Similarity	NPD5208	Approved
0.7176	Intermediate Similarity	NPD3668	Phase 3
0.7176	Intermediate Similarity	NPD4786	Approved
0.7176	Intermediate Similarity	NPD4197	Approved
0.7159	Intermediate Similarity	NPD4753	Phase 2
0.7159	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD6080	Approved
0.7159	Intermediate Similarity	NPD6904	Approved
0.7159	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD4137	Phase 3
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4202	Approved
0.7093	Intermediate Similarity	NPD5329	Approved
0.7093	Intermediate Similarity	NPD1694	Approved
0.7079	Intermediate Similarity	NPD5207	Approved
0.7079	Intermediate Similarity	NPD5692	Phase 3
0.7073	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4747	Approved
0.7051	Intermediate Similarity	NPD4691	Approved
0.7033	Intermediate Similarity	NPD5282	Discontinued
0.7033	Intermediate Similarity	NPD6001	Approved
0.7024	Intermediate Similarity	NPD5369	Approved
0.7011	Intermediate Similarity	NPD4694	Approved
0.7011	Intermediate Similarity	NPD4688	Approved
0.7011	Intermediate Similarity	NPD4693	Phase 3
0.7011	Intermediate Similarity	NPD4690	Approved
0.7011	Intermediate Similarity	NPD5690	Phase 2
0.7011	Intermediate Similarity	NPD5205	Approved
0.7011	Intermediate Similarity	NPD4689	Approved
0.7011	Intermediate Similarity	NPD6098	Approved
0.7011	Intermediate Similarity	NPD4138	Approved
0.7011	Intermediate Similarity	NPD5280	Approved
0.701	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD5693	Phase 1
0.7	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD6050	Approved
0.6989	Remote Similarity	NPD6083	Phase 2
0.6989	Remote Similarity	NPD6084	Phase 2
0.6974	Remote Similarity	NPD7331	Phase 2
0.6966	Remote Similarity	NPD1695	Approved
0.6962	Remote Similarity	NPD5276	Approved
0.6941	Remote Similarity	NPD6435	Approved
0.6941	Remote Similarity	NPD5209	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6915	Remote Similarity	NPD5696	Approved
0.6889	Remote Similarity	NPD5785	Approved
0.6867	Remote Similarity	NPD3617	Approved
0.6854	Remote Similarity	NPD4518	Approved
0.6842	Remote Similarity	NPD7341	Phase 2
0.6818	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4755	Approved
0.679	Remote Similarity	NPD4058	Approved
0.679	Remote Similarity	NPD4687	Approved
0.679	Remote Similarity	NPD5733	Approved
0.6774	Remote Similarity	NPD5210	Approved
0.6774	Remote Similarity	NPD4629	Approved
0.6742	Remote Similarity	NPD3573	Approved
0.6706	Remote Similarity	NPD5368	Approved
0.6706	Remote Similarity	NPD4695	Discontinued
0.6705	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5363	Approved
0.6703	Remote Similarity	NPD4096	Approved
0.6702	Remote Similarity	NPD4697	Phase 3
0.6702	Remote Similarity	NPD5222	Approved
0.6702	Remote Similarity	NPD5221	Approved
0.6702	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6632	Remote Similarity	NPD5173	Approved
0.6632	Remote Similarity	NPD5959	Approved
0.663	Remote Similarity	NPD5284	Approved
0.663	Remote Similarity	NPD5281	Approved
0.6629	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD4623	Approved
0.66	Remote Similarity	NPD5697	Approved
0.66	Remote Similarity	NPD5701	Approved
0.6598	Remote Similarity	NPD5223	Approved
0.6596	Remote Similarity	NPD5654	Approved
0.6596	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4195	Approved
0.6585	Remote Similarity	NPD6924	Approved
0.6585	Remote Similarity	NPD6926	Approved
0.6582	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5133	Approved
0.6552	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD4270	Approved
0.6535	Remote Similarity	NPD6881	Approved
0.6535	Remote Similarity	NPD6899	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6535	Remote Similarity	NPD7320	Approved
0.6531	Remote Similarity	NPD5224	Approved
0.6531	Remote Similarity	NPD5226	Approved
0.6531	Remote Similarity	NPD5225	Approved
0.6531	Remote Similarity	NPD4633	Approved
0.6531	Remote Similarity	NPD5211	Phase 2
0.6506	Remote Similarity	NPD8039	Approved
0.6477	Remote Similarity	NPD7154	Phase 3
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6373	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.6465	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD5174	Approved
0.6465	Remote Similarity	NPD5175	Approved
0.6458	Remote Similarity	NPD7902	Approved
0.6452	Remote Similarity	NPD7515	Phase 2
0.6444	Remote Similarity	NPD5786	Approved
0.6437	Remote Similarity	NPD4139	Approved
0.6437	Remote Similarity	NPD4692	Approved
0.6436	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD6933	Approved
0.6408	Remote Similarity	NPD7102	Approved
0.6408	Remote Similarity	NPD6883	Approved
0.6408	Remote Similarity	NPD7290	Approved
0.64	Remote Similarity	NPD5141	Approved
0.6392	Remote Similarity	NPD7638	Approved
0.6355	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD6847	Approved
0.6346	Remote Similarity	NPD6869	Approved
0.6346	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD8130	Phase 1
0.6346	Remote Similarity	NPD6649	Approved
0.6346	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD6617	Approved
0.6344	Remote Similarity	NPD6698	Approved
0.6344	Remote Similarity	NPD46	Approved
0.6337	Remote Similarity	NPD4768	Approved
0.6337	Remote Similarity	NPD4767	Approved
0.6329	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7640	Approved
0.6327	Remote Similarity	NPD7639	Approved
0.6322	Remote Similarity	NPD4820	Approved
0.6322	Remote Similarity	NPD4819	Approved
0.6322	Remote Similarity	NPD4821	Approved
0.6322	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4252	Approved
0.6322	Remote Similarity	NPD4822	Approved
0.63	Remote Similarity	NPD6052	Approved
0.6292	Remote Similarity	NPD6695	Phase 3
0.6286	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD8297	Approved
0.6277	Remote Similarity	NPD6411	Approved
0.6267	Remote Similarity	NPD287	Approved
0.625	Remote Similarity	NPD6371	Approved
0.6237	Remote Similarity	NPD6051	Approved
0.6235	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4730	Approved
0.6214	Remote Similarity	NPD5128	Approved
0.6214	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1696	Phase 3
0.6145	Remote Similarity	NPD5777	Approved
0.6136	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6931	Approved
0.6136	Remote Similarity	NPD6930	Phase 2
0.6136	Remote Similarity	NPD7525	Registered
0.6118	Remote Similarity	NPD6942	Approved
0.6118	Remote Similarity	NPD7339	Approved
0.6117	Remote Similarity	NPD6614	Approved
0.6111	Remote Similarity	NPD6274	Approved
0.6111	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6105	Remote Similarity	NPD8034	Phase 2

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