NPASS Compound

Structure

NPC108045 OpenBabel07101718242D 26 28 0 0 1 0 0 0 0 0999 V2000 3.8722 -0.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3361 -1.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3139 -4.3303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7070 -3.2831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9357 -2.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7631 -0.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1586 -3.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5871 -1.0888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0969 -3.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 -0.5287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3506 -2.7848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6084 -3.3999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3708 -1.0207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2462 -3.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0228 -2.3707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9459 -1.9851 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3135 -2.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4424 -1.8237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9041 -1.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7632 -2.9332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8362 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9708 -2.1879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2616 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3905 -1.6410 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 4 15 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 6 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 20 22 1 6 0 0 0 20 26 1 0 0 0 0 21 5 1 6 0 0 0 22 6 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	388.014
LogP:	4.056
LogD:	3.761
LogS:	-4.747
# Rotatable Bonds:	2
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	5.115
Fsp3:	0.727
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:	-4.661
MDCK Permeability:	2.3488502847612835e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.658
30% Bioavailability (F30%):	0.69

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.472
Plasma Protein Binding (PPB):	88.6767807006836%
Volume Distribution (VD):	0.786
Pgp-substrate:	15.744585037231445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.531

ADMET: Excretion

Clearance (CL):	6.471
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.523
Drug-inuced Liver Injury (DILI):	0.669
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.953
Carcinogencity:	0.77
Eye Corrosion:	0.789
Eye Irritation:	0.529
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC108045

Natural Product ID:	NPC108045
*Common Name:**	BBQSAOCTCFTPCK-STWNPLFQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BBQSAOCTCFTPCK-STWNPLFQSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-13(2)19-16-8-10-22(6)20(26-22)18(25-15(4)23)11-14(3)7-9-21(16,5)12-17(19)24/h7,16,18,20H,8-12H2,1-6H3/b14-7+/t16-,18+,20+,21-,22+/m1/s1
SMILES:	CC(=C1[C@H]2CC[C@@]3(C)[C@H]([C@H](C/C(=C/C[C@]2(C)CC1=O)/C)OC(=O)C)O3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095333
PubChem CID:	46887712
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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	33300.0	nM	PMID[447788]

☑ 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 NPC108045 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	211
0.1-0.2	1414
0.2-0.3	6253
0.3-0.4	15196
0.4-0.5	7848
0.5-0.6	6925
0.6-0.7	4202
0.7-0.8	619
0.8-0.85	21
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475622
0.8831	High Similarity	NPC469691
0.8831	High Similarity	NPC167049
0.869	High Similarity	NPC261253
0.869	High Similarity	NPC474045
0.8481	Intermediate Similarity	NPC469669
0.8481	Intermediate Similarity	NPC469678
0.8481	Intermediate Similarity	NPC475771
0.8471	Intermediate Similarity	NPC469676
0.8462	Intermediate Similarity	NPC107783
0.8462	Intermediate Similarity	NPC92909
0.8293	Intermediate Similarity	NPC469620
0.8293	Intermediate Similarity	NPC469690
0.8242	Intermediate Similarity	NPC477354
0.8148	Intermediate Similarity	NPC226242
0.8111	Intermediate Similarity	NPC477361
0.8111	Intermediate Similarity	NPC202824
0.8095	Intermediate Similarity	NPC255580
0.8095	Intermediate Similarity	NPC39411
0.8065	Intermediate Similarity	NPC471582
0.8065	Intermediate Similarity	NPC477355
0.7975	Intermediate Similarity	NPC475310
0.7955	Intermediate Similarity	NPC471739
0.7952	Intermediate Similarity	NPC474056
0.7895	Intermediate Similarity	NPC477356
0.7882	Intermediate Similarity	NPC141810
0.7882	Intermediate Similarity	NPC471325
0.7857	Intermediate Similarity	NPC617
0.7857	Intermediate Similarity	NPC471740
0.7848	Intermediate Similarity	NPC329656
0.7841	Intermediate Similarity	NPC195640
0.7831	Intermediate Similarity	NPC15975
0.7831	Intermediate Similarity	NPC195785
0.7831	Intermediate Similarity	NPC476264
0.7831	Intermediate Similarity	NPC476325
0.7816	Intermediate Similarity	NPC475796
0.7805	Intermediate Similarity	NPC474419
0.7805	Intermediate Similarity	NPC475861
0.7802	Intermediate Similarity	NPC221282
0.7791	Intermediate Similarity	NPC35556
0.7778	Intermediate Similarity	NPC470237
0.7778	Intermediate Similarity	NPC83423
0.7766	Intermediate Similarity	NPC87090
0.7765	Intermediate Similarity	NPC304795
0.7742	Intermediate Similarity	NPC472469
0.7727	Intermediate Similarity	NPC323765
0.7727	Intermediate Similarity	NPC78089
0.7701	Intermediate Similarity	NPC475989
0.7701	Intermediate Similarity	NPC193198
0.7701	Intermediate Similarity	NPC53867
0.7692	Intermediate Similarity	NPC475748
0.7692	Intermediate Similarity	NPC475965
0.7692	Intermediate Similarity	NPC474842
0.7692	Intermediate Similarity	NPC51653
0.7683	Intermediate Similarity	NPC469643
0.7683	Intermediate Similarity	NPC469641
0.7674	Intermediate Similarity	NPC207188
0.7674	Intermediate Similarity	NPC286229
0.7667	Intermediate Similarity	NPC476707
0.7667	Intermediate Similarity	NPC476706
0.766	Intermediate Similarity	NPC471775
0.7647	Intermediate Similarity	NPC471299
0.7647	Intermediate Similarity	NPC622
0.7647	Intermediate Similarity	NPC276647
0.7647	Intermediate Similarity	NPC178277
0.7647	Intermediate Similarity	NPC469608
0.764	Intermediate Similarity	NPC107787
0.7634	Intermediate Similarity	NPC174051
0.7634	Intermediate Similarity	NPC473431
0.7634	Intermediate Similarity	NPC473280
0.7634	Intermediate Similarity	NPC473435
0.7634	Intermediate Similarity	NPC67831
0.7634	Intermediate Similarity	NPC471078
0.7634	Intermediate Similarity	NPC124207
0.7629	Intermediate Similarity	NPC118405
0.7625	Intermediate Similarity	NPC477448
0.7625	Intermediate Similarity	NPC22301
0.7625	Intermediate Similarity	NPC477449
0.7619	Intermediate Similarity	NPC186109
0.7614	Intermediate Similarity	NPC115786
0.7614	Intermediate Similarity	NPC165287
0.7614	Intermediate Similarity	NPC100391
0.7609	Intermediate Similarity	NPC262870
0.759	Intermediate Similarity	NPC93213
0.759	Intermediate Similarity	NPC113639
0.759	Intermediate Similarity	NPC324762
0.7586	Intermediate Similarity	NPC321289
0.7586	Intermediate Similarity	NPC327969
0.7582	Intermediate Similarity	NPC151770
0.7582	Intermediate Similarity	NPC477215
0.7582	Intermediate Similarity	NPC476388
0.7579	Intermediate Similarity	NPC110937
0.7576	Intermediate Similarity	NPC470975
0.7576	Intermediate Similarity	NPC103088
0.7576	Intermediate Similarity	NPC470979
0.7558	Intermediate Similarity	NPC103634
0.7556	Intermediate Similarity	NPC231889
0.7553	Intermediate Similarity	NPC33473
0.7549	Intermediate Similarity	NPC475495
0.7531	Intermediate Similarity	NPC472955
0.7529	Intermediate Similarity	NPC474005
0.7529	Intermediate Similarity	NPC128276
0.7528	Intermediate Similarity	NPC474547
0.7527	Intermediate Similarity	NPC476598
0.7527	Intermediate Similarity	NPC477615
0.7527	Intermediate Similarity	NPC469315
0.7527	Intermediate Similarity	NPC476597
0.7526	Intermediate Similarity	NPC476134
0.7526	Intermediate Similarity	NPC469327
0.7526	Intermediate Similarity	NPC101067
0.75	Intermediate Similarity	NPC251385
0.75	Intermediate Similarity	NPC222303
0.75	Intermediate Similarity	NPC478004
0.75	Intermediate Similarity	NPC470192
0.75	Intermediate Similarity	NPC252295
0.75	Intermediate Similarity	NPC471610
0.75	Intermediate Similarity	NPC301525
0.75	Intermediate Similarity	NPC475842
0.75	Intermediate Similarity	NPC158388
0.75	Intermediate Similarity	NPC478003
0.75	Intermediate Similarity	NPC471601
0.75	Intermediate Similarity	NPC475947
0.75	Intermediate Similarity	NPC49342
0.7476	Intermediate Similarity	NPC473522
0.7476	Intermediate Similarity	NPC477093
0.7476	Intermediate Similarity	NPC475277
0.7475	Intermediate Similarity	NPC169843
0.7474	Intermediate Similarity	NPC151725
0.7474	Intermediate Similarity	NPC471777
0.7474	Intermediate Similarity	NPC122324
0.7474	Intermediate Similarity	NPC106425
0.7473	Intermediate Similarity	NPC475902
0.7473	Intermediate Similarity	NPC476704
0.7473	Intermediate Similarity	NPC80335
0.7471	Intermediate Similarity	NPC25684
0.7471	Intermediate Similarity	NPC301477
0.7471	Intermediate Similarity	NPC476988
0.7471	Intermediate Similarity	NPC475481
0.7471	Intermediate Similarity	NPC281949
0.7471	Intermediate Similarity	NPC79277
0.7471	Intermediate Similarity	NPC475665
0.747	Intermediate Similarity	NPC474758
0.7449	Intermediate Similarity	NPC471757
0.7449	Intermediate Similarity	NPC78127
0.7449	Intermediate Similarity	NPC105725
0.7449	Intermediate Similarity	NPC473163
0.7447	Intermediate Similarity	NPC318332
0.7447	Intermediate Similarity	NPC473316
0.7447	Intermediate Similarity	NPC476596
0.7447	Intermediate Similarity	NPC38830
0.7447	Intermediate Similarity	NPC473330
0.7444	Intermediate Similarity	NPC104961
0.7444	Intermediate Similarity	NPC70555
0.7444	Intermediate Similarity	NPC220478
0.7444	Intermediate Similarity	NPC70422
0.7444	Intermediate Similarity	NPC264127
0.7444	Intermediate Similarity	NPC50637
0.7442	Intermediate Similarity	NPC476177
0.7442	Intermediate Similarity	NPC268502
0.7442	Intermediate Similarity	NPC254996
0.7442	Intermediate Similarity	NPC308545
0.7442	Intermediate Similarity	NPC182550
0.7442	Intermediate Similarity	NPC82488
0.7436	Intermediate Similarity	NPC287744
0.7436	Intermediate Similarity	NPC140233
0.7426	Intermediate Similarity	NPC475418
0.7426	Intermediate Similarity	NPC318363
0.7426	Intermediate Similarity	NPC473482
0.7423	Intermediate Similarity	NPC167974
0.7419	Intermediate Similarity	NPC218301
0.7419	Intermediate Similarity	NPC123177
0.7419	Intermediate Similarity	NPC150978
0.7419	Intermediate Similarity	NPC476705
0.7419	Intermediate Similarity	NPC74103
0.7419	Intermediate Similarity	NPC70595
0.7416	Intermediate Similarity	NPC320801
0.7416	Intermediate Similarity	NPC72464
0.7412	Intermediate Similarity	NPC476794
0.7412	Intermediate Similarity	NPC57744
0.7412	Intermediate Similarity	NPC470240
0.7407	Intermediate Similarity	NPC144511
0.7407	Intermediate Similarity	NPC296522
0.74	Intermediate Similarity	NPC291643
0.74	Intermediate Similarity	NPC469874
0.7391	Intermediate Similarity	NPC469866
0.7391	Intermediate Similarity	NPC166919
0.7391	Intermediate Similarity	NPC305039
0.7391	Intermediate Similarity	NPC471342
0.7386	Intermediate Similarity	NPC240302
0.7386	Intermediate Similarity	NPC475936
0.7386	Intermediate Similarity	NPC145963
0.7381	Intermediate Similarity	NPC244166
0.7363	Intermediate Similarity	NPC476600
0.7363	Intermediate Similarity	NPC197333
0.7363	Intermediate Similarity	NPC475703
0.7363	Intermediate Similarity	NPC474765
0.7363	Intermediate Similarity	NPC478144
0.7363	Intermediate Similarity	NPC167877
0.7363	Intermediate Similarity	NPC478145
0.7356	Intermediate Similarity	NPC47747

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 NPC108045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	2049
0.2-0.3	4073
0.3-0.4	1929
0.4-0.5	492
0.5-0.6	254
0.6-0.7	143
0.7-0.8	17
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
0.7841	Intermediate Similarity	NPD6684	Approved
0.7841	Intermediate Similarity	NPD7146	Approved
0.7841	Intermediate Similarity	NPD7521	Approved
0.7841	Intermediate Similarity	NPD7334	Approved
0.7841	Intermediate Similarity	NPD6409	Approved
0.7841	Intermediate Similarity	NPD5330	Approved
0.7667	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD5737	Approved
0.7667	Intermediate Similarity	NPD6903	Approved
0.7471	Intermediate Similarity	NPD5369	Approved
0.7396	Intermediate Similarity	NPD6084	Phase 2
0.7396	Intermediate Similarity	NPD6083	Phase 2
0.7391	Intermediate Similarity	NPD6673	Approved
0.7391	Intermediate Similarity	NPD6904	Approved
0.7391	Intermediate Similarity	NPD6080	Approved
0.7386	Intermediate Similarity	NPD6435	Approved
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7368	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6698	Approved
0.7312	Intermediate Similarity	NPD5785	Approved
0.7312	Intermediate Similarity	NPD46	Approved
0.7234	Intermediate Similarity	NPD6050	Approved
0.7228	Intermediate Similarity	NPD6008	Approved
0.7204	Intermediate Similarity	NPD1695	Approved
0.7196	Intermediate Similarity	NPD7115	Discovery
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5368	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD5363	Approved
0.7128	Intermediate Similarity	NPD5692	Phase 3
0.7115	Intermediate Similarity	NPD6371	Approved
0.7111	Intermediate Similarity	NPD5362	Discontinued
0.7111	Intermediate Similarity	NPD7154	Phase 3
0.7097	Intermediate Similarity	NPD5208	Approved
0.7065	Intermediate Similarity	NPD6098	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7053	Intermediate Similarity	NPD5693	Phase 1
0.7053	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.7	Intermediate Similarity	NPD5209	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6966	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4822	Approved
0.6966	Remote Similarity	NPD4821	Approved
0.6966	Remote Similarity	NPD4820	Approved
0.6966	Remote Similarity	NPD4819	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6947	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6914	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6001	Approved
0.6907	Remote Similarity	NPD5282	Discontinued
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7748	Approved
0.6907	Remote Similarity	NPD7900	Approved
0.6882	Remote Similarity	NPD5786	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6848	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD4786	Approved
0.6848	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD3666	Approved
0.6848	Remote Similarity	NPD3665	Phase 1
0.6842	Remote Similarity	NPD4753	Phase 2
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6827	Remote Similarity	NPD6412	Phase 2
0.6827	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3667	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6778	Remote Similarity	NPD4252	Approved
0.6771	Remote Similarity	NPD7838	Discovery
0.6742	Remote Similarity	NPD4271	Approved
0.6742	Remote Similarity	NPD4268	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD6650	Approved
0.6702	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD3618	Phase 1
0.6701	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD5284	Approved
0.6701	Remote Similarity	NPD5281	Approved
0.67	Remote Similarity	NPD5959	Approved
0.67	Remote Similarity	NPD7902	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5654	Approved
0.6634	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD3573	Approved
0.663	Remote Similarity	NPD4221	Approved
0.663	Remote Similarity	NPD4223	Phase 3
0.6604	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD6686	Approved
0.6596	Remote Similarity	NPD5329	Approved
0.6591	Remote Similarity	NPD8039	Approved
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6559	Remote Similarity	NPD5332	Approved
0.6559	Remote Similarity	NPD5331	Approved
0.6538	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD4755	Approved
0.6531	Remote Similarity	NPD7637	Suspended
0.6531	Remote Similarity	NPD7983	Approved
0.6531	Remote Similarity	NPD6079	Approved
0.6522	Remote Similarity	NPD4790	Discontinued
0.6509	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5210	Approved
0.65	Remote Similarity	NPD4629	Approved
0.6495	Remote Similarity	NPD6051	Approved
0.6489	Remote Similarity	NPD4197	Approved
0.6465	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD5778	Approved
0.6465	Remote Similarity	NPD4202	Approved
0.6458	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD7524	Approved
0.6458	Remote Similarity	NPD4250	Approved
0.6455	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD7331	Phase 2
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4695	Discontinued
0.6408	Remote Similarity	NPD5286	Approved
0.6408	Remote Similarity	NPD4700	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6408	Remote Similarity	NPD6648	Approved
0.6404	Remote Similarity	NPD6319	Approved
0.6395	Remote Similarity	NPD4137	Phase 3
0.6392	Remote Similarity	NPD4518	Approved
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6695	Phase 3
0.6379	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6053	Discontinued
0.6355	Remote Similarity	NPD6614	Approved
0.6354	Remote Similarity	NPD4689	Approved
0.6354	Remote Similarity	NPD4693	Phase 3
0.6354	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4688	Approved
0.6354	Remote Similarity	NPD4249	Approved
0.6354	Remote Similarity	NPD5280	Approved
0.6354	Remote Similarity	NPD4690	Approved
0.6354	Remote Similarity	NPD5690	Phase 2
0.6354	Remote Similarity	NPD5205	Approved
0.6354	Remote Similarity	NPD4694	Approved
0.6354	Remote Similarity	NPD4138	Approved
0.6346	Remote Similarity	NPD5344	Discontinued
0.6339	Remote Similarity	NPD6274	Approved
0.6333	Remote Similarity	NPD6933	Approved
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7492	Approved
0.6322	Remote Similarity	NPD4691	Approved
0.6322	Remote Similarity	NPD4747	Approved
0.6316	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7100	Approved
0.631	Remote Similarity	NPD7341	Phase 2
0.6292	Remote Similarity	NPD5733	Approved
0.6292	Remote Similarity	NPD6924	Approved
0.6292	Remote Similarity	NPD6926	Approved
0.6286	Remote Similarity	NPD5225	Approved
0.6286	Remote Similarity	NPD5224	Approved
0.6286	Remote Similarity	NPD5211	Phase 2
0.6286	Remote Similarity	NPD5226	Approved
0.6286	Remote Similarity	NPD4633	Approved
0.6283	Remote Similarity	NPD6009	Approved
0.6275	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5222	Approved
0.6275	Remote Similarity	NPD4697	Phase 3
0.6275	Remote Similarity	NPD5221	Approved
0.6271	Remote Similarity	NPD6616	Approved
0.6261	Remote Similarity	NPD6054	Approved
0.6261	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD5276	Approved
0.625	Remote Similarity	NPD5777	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