NPASS Compound

Structure

NPC469608 OpenBabel07101719522D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.9553 -5.2096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5543 -5.7644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5455 -2.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5347 -4.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6574 -0.3440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1143 -3.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4881 -1.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0167 -3.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7317 -0.5085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2088 -2.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4255 -1.7539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0403 -5.0512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2368 -3.4082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1734 -3.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8332 -1.9091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2800 -4.1797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3372 -2.6783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6575 -2.8209 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8042 -0.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9033 -4.5005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5350 -2.5172 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 12 1 0 0 0 0 2 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 13 17 1 0 0 0 0 13 18 1 1 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 19 1 1 0 0 0 15 22 1 0 0 0 0 16 20 1 6 0 0 0 16 23 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	4.065
LogD:	3.487
LogS:	-4.881
# Rotatable Bonds:	0
TPSA:	42.13
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.496
Synthetic Accessibility Score:	5.214
Fsp3:	0.85
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:	-4.706
MDCK Permeability:	1.9707216779352166e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	88.97386932373047%
Volume Distribution (VD):	1.673
Pgp-substrate:	6.083596229553223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.583
CYP3A4-substrate:	0.666

ADMET: Excretion

Clearance (CL):	9.379
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.519
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.941
Carcinogencity:	0.735
Eye Corrosion:	0.928
Eye Irritation:	0.739
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: NPC469608

Natural Product ID:	NPC469608
*Common Name:**	YUVBUOIJKQKXOJ-KNLVXHHQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YUVBUOIJKQKXOJ-KNLVXHHQSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-12(2)17-13-6-8-19(4)15(22-19)7-9-20(5)16(23-20)11-18(13,3)10-14(17)21/h13,15-16H,6-11H2,1-5H3/t13-,15+,16-,18+,19+,20-/m1/s1
SMILES:	CC(=C1C(=O)C[C@@]2([C@@H]1CC[C@]1(C)O[C@H]1CC[C@@]1([C@@H](C2)O1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094089
PubChem CID:	46887665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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	=	37700.0	nM	PMID[493134]

☑ 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 NPC469608 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	253
0.1-0.2	2321
0.2-0.3	9382
0.3-0.4	15083
0.4-0.5	8090
0.5-0.6	6237
0.6-0.7	1229
0.7-0.8	93
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8553	High Similarity	NPC469691
0.8553	High Similarity	NPC167049
0.8481	Intermediate Similarity	NPC80999
0.8434	Intermediate Similarity	NPC469676
0.8333	Intermediate Similarity	NPC226242
0.8205	Intermediate Similarity	NPC469678
0.8205	Intermediate Similarity	NPC475771
0.8205	Intermediate Similarity	NPC469669
0.8182	Intermediate Similarity	NPC107783
0.8182	Intermediate Similarity	NPC92909
0.8	Intermediate Similarity	NPC261253
0.8	Intermediate Similarity	NPC474045
0.7901	Intermediate Similarity	NPC474056
0.7765	Intermediate Similarity	NPC475796
0.7683	Intermediate Similarity	NPC207186
0.7674	Intermediate Similarity	NPC474547
0.7647	Intermediate Similarity	NPC475622
0.7647	Intermediate Similarity	NPC108045
0.759	Intermediate Similarity	NPC469690
0.759	Intermediate Similarity	NPC469620
0.7556	Intermediate Similarity	NPC221282
0.7442	Intermediate Similarity	NPC272814
0.7439	Intermediate Similarity	NPC469646
0.7419	Intermediate Similarity	NPC477354
0.7349	Intermediate Similarity	NPC186109
0.7342	Intermediate Similarity	NPC261398
0.7342	Intermediate Similarity	NPC477448
0.7342	Intermediate Similarity	NPC477449
0.7263	Intermediate Similarity	NPC477355
0.7253	Intermediate Similarity	NPC62815
0.7229	Intermediate Similarity	NPC142759
0.7229	Intermediate Similarity	NPC473437
0.7229	Intermediate Similarity	NPC141346
0.7229	Intermediate Similarity	NPC124289
0.7229	Intermediate Similarity	NPC25908
0.7229	Intermediate Similarity	NPC115719
0.7222	Intermediate Similarity	NPC476704
0.7209	Intermediate Similarity	NPC207188
0.7195	Intermediate Similarity	NPC469641
0.7195	Intermediate Similarity	NPC469643
0.7176	Intermediate Similarity	NPC276647
0.7176	Intermediate Similarity	NPC622
0.7174	Intermediate Similarity	NPC290651
0.7159	Intermediate Similarity	NPC32565
0.7159	Intermediate Similarity	NPC120726
0.7143	Intermediate Similarity	NPC32922
0.7143	Intermediate Similarity	NPC166919
0.7143	Intermediate Similarity	NPC97032
0.7128	Intermediate Similarity	NPC37408
0.7126	Intermediate Similarity	NPC145963
0.7113	Intermediate Similarity	NPC477356
0.7111	Intermediate Similarity	NPC231889
0.7111	Intermediate Similarity	NPC475703
0.7108	Intermediate Similarity	NPC474011
0.7108	Intermediate Similarity	NPC216791
0.7097	Intermediate Similarity	NPC475488
0.7097	Intermediate Similarity	NPC202824
0.7097	Intermediate Similarity	NPC477361
0.7079	Intermediate Similarity	NPC96621
0.7071	Intermediate Similarity	NPC169843
0.7065	Intermediate Similarity	NPC469718
0.7065	Intermediate Similarity	NPC312042
0.7065	Intermediate Similarity	NPC329857
0.7053	Intermediate Similarity	NPC58052
0.7053	Intermediate Similarity	NPC111684
0.7045	Intermediate Similarity	NPC170377
0.7045	Intermediate Similarity	NPC475842
0.7033	Intermediate Similarity	NPC476706
0.7033	Intermediate Similarity	NPC476707
0.7033	Intermediate Similarity	NPC224652
0.7021	Intermediate Similarity	NPC90453
0.7021	Intermediate Similarity	NPC476267
0.7	Intermediate Similarity	NPC469688
0.7	Intermediate Similarity	NPC232156
0.7	Intermediate Similarity	NPC137253
0.7	Intermediate Similarity	NPC470346
0.699	Remote Similarity	NPC475495
0.6989	Remote Similarity	NPC20713
0.6979	Remote Similarity	NPC20078
0.6979	Remote Similarity	NPC473574
0.6977	Remote Similarity	NPC476177
0.6977	Remote Similarity	NPC229204
0.6977	Remote Similarity	NPC261125
0.6977	Remote Similarity	NPC181195
0.697	Remote Similarity	NPC123505
0.6966	Remote Similarity	NPC109512
0.6966	Remote Similarity	NPC138647
0.6966	Remote Similarity	NPC470238
0.6957	Remote Similarity	NPC151770
0.6951	Remote Similarity	NPC144627
0.6941	Remote Similarity	NPC276769
0.6939	Remote Similarity	NPC181645
0.6932	Remote Similarity	NPC133844
0.6931	Remote Similarity	NPC471601
0.6923	Remote Similarity	NPC475277
0.6923	Remote Similarity	NPC140233
0.6923	Remote Similarity	NPC471739
0.6923	Remote Similarity	NPC197333
0.6923	Remote Similarity	NPC287744
0.6923	Remote Similarity	NPC473522
0.6923	Remote Similarity	NPC270270
0.6923	Remote Similarity	NPC477093
0.6915	Remote Similarity	NPC135776
0.6915	Remote Similarity	NPC125180
0.6907	Remote Similarity	NPC470188
0.6907	Remote Similarity	NPC208233
0.6907	Remote Similarity	NPC109556
0.6905	Remote Similarity	NPC475861
0.6897	Remote Similarity	NPC474510
0.6897	Remote Similarity	NPC47747
0.6889	Remote Similarity	NPC235792
0.6889	Remote Similarity	NPC323765
0.6882	Remote Similarity	NPC478257
0.6882	Remote Similarity	NPC475748
0.6882	Remote Similarity	NPC478258
0.6875	Remote Similarity	NPC476275
0.686	Remote Similarity	NPC23187
0.6854	Remote Similarity	NPC474472
0.6854	Remote Similarity	NPC257358
0.6854	Remote Similarity	NPC54468
0.6854	Remote Similarity	NPC473629
0.6842	Remote Similarity	NPC140543
0.6842	Remote Similarity	NPC473330
0.6842	Remote Similarity	NPC318332
0.6842	Remote Similarity	NPC471147
0.6842	Remote Similarity	NPC259261
0.6842	Remote Similarity	NPC298919
0.6842	Remote Similarity	NPC473316
0.6837	Remote Similarity	NPC112167
0.6835	Remote Similarity	NPC61473
0.6832	Remote Similarity	NPC470979
0.6832	Remote Similarity	NPC470975
0.6832	Remote Similarity	NPC103088
0.6829	Remote Similarity	NPC280256
0.6824	Remote Similarity	NPC215481
0.6818	Remote Similarity	NPC136150
0.6818	Remote Similarity	NPC255580
0.6818	Remote Similarity	NPC478262
0.6818	Remote Similarity	NPC39411
0.6813	Remote Similarity	NPC70422
0.6813	Remote Similarity	NPC470345
0.6813	Remote Similarity	NPC50637
0.6813	Remote Similarity	NPC104961
0.6813	Remote Similarity	NPC122502
0.6813	Remote Similarity	NPC195640
0.6813	Remote Similarity	NPC70555
0.6809	Remote Similarity	NPC286341
0.6809	Remote Similarity	NPC191339
0.6809	Remote Similarity	NPC476705
0.6809	Remote Similarity	NPC478243
0.6809	Remote Similarity	NPC472953
0.6809	Remote Similarity	NPC478244
0.6809	Remote Similarity	NPC218301
0.6804	Remote Similarity	NPC477949
0.6804	Remote Similarity	NPC111187
0.6804	Remote Similarity	NPC87090
0.6804	Remote Similarity	NPC190080
0.6804	Remote Similarity	NPC187159
0.6782	Remote Similarity	NPC617
0.6782	Remote Similarity	NPC268502
0.6782	Remote Similarity	NPC136033
0.6782	Remote Similarity	NPC254996
0.6782	Remote Similarity	NPC471740
0.6778	Remote Similarity	NPC471343
0.6774	Remote Similarity	NPC186688
0.6774	Remote Similarity	NPC78008
0.6774	Remote Similarity	NPC4986
0.6771	Remote Similarity	NPC200702
0.6771	Remote Similarity	NPC474947
0.6768	Remote Similarity	NPC475099
0.6768	Remote Similarity	NPC264477
0.6768	Remote Similarity	NPC477511
0.6768	Remote Similarity	NPC237190
0.6768	Remote Similarity	NPC471401
0.6765	Remote Similarity	NPC470192
0.6765	Remote Similarity	NPC473165
0.6747	Remote Similarity	NPC469737
0.6744	Remote Similarity	NPC195785
0.6744	Remote Similarity	NPC15975
0.6742	Remote Similarity	NPC475936
0.6742	Remote Similarity	NPC70479
0.6739	Remote Similarity	NPC118601
0.6739	Remote Similarity	NPC469322
0.6737	Remote Similarity	NPC153590
0.6737	Remote Similarity	NPC109414
0.6737	Remote Similarity	NPC477615
0.6737	Remote Similarity	NPC212486
0.6735	Remote Similarity	NPC264378
0.6735	Remote Similarity	NPC222303
0.6735	Remote Similarity	NPC471582
0.6731	Remote Similarity	NPC50223
0.6731	Remote Similarity	NPC76084
0.6731	Remote Similarity	NPC41551
0.6711	Remote Similarity	NPC94991
0.6711	Remote Similarity	NPC266295
0.6707	Remote Similarity	NPC469677
0.6706	Remote Similarity	NPC251435
0.6706	Remote Similarity	NPC474419
0.6705	Remote Similarity	NPC304795
0.6705	Remote Similarity	NPC73052

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 NPC469608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	3168
0.2-0.3	3962
0.3-0.4	1184
0.4-0.5	297
0.5-0.6	248
0.6-0.7	31
0.7-0.8	0
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
0.7172	Intermediate Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD5282	Discontinued
0.6835	Remote Similarity	NPD7341	Phase 2
0.6813	Remote Similarity	NPD7334	Approved
0.6813	Remote Similarity	NPD6684	Approved
0.6813	Remote Similarity	NPD7521	Approved
0.6813	Remote Similarity	NPD6409	Approved
0.6813	Remote Similarity	NPD5330	Approved
0.6813	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD1695	Approved
0.6703	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6602	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD3666	Approved
0.6593	Remote Similarity	NPD3133	Approved
0.6593	Remote Similarity	NPD3665	Phase 1
0.6556	Remote Similarity	NPD6435	Approved
0.6489	Remote Similarity	NPD5737	Approved
0.6489	Remote Similarity	NPD6672	Approved
0.6477	Remote Similarity	NPD3617	Approved
0.6476	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4755	Approved
0.6458	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD5279	Phase 3
0.6415	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4202	Approved
0.6374	Remote Similarity	NPD3667	Approved
0.6374	Remote Similarity	NPD4223	Phase 3
0.6374	Remote Similarity	NPD4221	Approved
0.6346	Remote Similarity	NPD7128	Approved
0.6346	Remote Similarity	NPD6675	Approved
0.6346	Remote Similarity	NPD6402	Approved
0.6346	Remote Similarity	NPD5739	Approved
0.6344	Remote Similarity	NPD1694	Approved
0.6341	Remote Similarity	NPD7331	Phase 2
0.6337	Remote Similarity	NPD4696	Approved
0.6337	Remote Similarity	NPD5285	Approved
0.6337	Remote Similarity	NPD5286	Approved
0.6337	Remote Similarity	NPD4700	Approved
0.6333	Remote Similarity	NPD5368	Approved
0.6327	Remote Similarity	NPD6001	Approved
0.6316	Remote Similarity	NPD5208	Approved
0.6286	Remote Similarity	NPD5697	Approved
0.6286	Remote Similarity	NPD5701	Approved
0.6286	Remote Similarity	NPD6412	Phase 2
0.6275	Remote Similarity	NPD5223	Approved
0.6263	Remote Similarity	NPD5695	Phase 3
0.6263	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6080	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6239	Remote Similarity	NPD4632	Approved
0.6237	Remote Similarity	NPD4197	Approved
0.6237	Remote Similarity	NPD3668	Phase 3
0.6237	Remote Similarity	NPD4786	Approved
0.6226	Remote Similarity	NPD7320	Approved
0.6226	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD6899	Approved
0.6226	Remote Similarity	NPD6881	Approved
0.6224	Remote Similarity	NPD6399	Phase 3
0.6214	Remote Similarity	NPD5225	Approved
0.6214	Remote Similarity	NPD5226	Approved
0.6214	Remote Similarity	NPD5211	Phase 2
0.6214	Remote Similarity	NPD5224	Approved
0.6214	Remote Similarity	NPD4633	Approved
0.6211	Remote Similarity	NPD3573	Approved
0.62	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5222	Approved
0.62	Remote Similarity	NPD5221	Approved
0.62	Remote Similarity	NPD4697	Phase 3
0.6196	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5207	Approved
0.6186	Remote Similarity	NPD6698	Approved
0.6186	Remote Similarity	NPD46	Approved
0.6186	Remote Similarity	NPD5692	Phase 3
0.617	Remote Similarity	NPD5329	Approved
0.6168	Remote Similarity	NPD6013	Approved
0.6168	Remote Similarity	NPD6373	Approved
0.6168	Remote Similarity	NPD6014	Approved
0.6168	Remote Similarity	NPD6012	Approved
0.6168	Remote Similarity	NPD6372	Approved
0.6154	Remote Similarity	NPD4754	Approved
0.6154	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD5175	Approved
0.6139	Remote Similarity	NPD5173	Approved
0.6139	Remote Similarity	NPD6084	Phase 2
0.6139	Remote Similarity	NPD6083	Phase 2
0.6122	Remote Similarity	NPD5694	Approved
0.6122	Remote Similarity	NPD6050	Approved
0.6122	Remote Similarity	NPD5693	Phase 1
0.6118	Remote Similarity	NPD4137	Phase 3
0.6111	Remote Similarity	NPD7290	Approved
0.6111	Remote Similarity	NPD4634	Approved
0.6111	Remote Similarity	NPD6883	Approved
0.6111	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7102	Approved
0.6111	Remote Similarity	NPD6371	Approved
0.6105	Remote Similarity	NPD5205	Approved
0.6105	Remote Similarity	NPD4690	Approved
0.6105	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5690	Phase 2
0.6105	Remote Similarity	NPD4694	Approved
0.6105	Remote Similarity	NPD4688	Approved
0.6105	Remote Similarity	NPD6098	Approved
0.6105	Remote Similarity	NPD5280	Approved
0.6105	Remote Similarity	NPD4689	Approved
0.6105	Remote Similarity	NPD4693	Phase 3
0.6105	Remote Similarity	NPD4138	Approved
0.6095	Remote Similarity	NPD5141	Approved
0.6087	Remote Similarity	NPD4139	Approved
0.6087	Remote Similarity	NPD4692	Approved
0.6087	Remote Similarity	NPD5369	Approved
0.6078	Remote Similarity	NPD5696	Approved
0.6078	Remote Similarity	NPD7638	Approved
0.6071	Remote Similarity	NPD6009	Approved
0.6055	Remote Similarity	NPD6649	Approved
0.6055	Remote Similarity	NPD6869	Approved
0.6055	Remote Similarity	NPD6847	Approved
0.6055	Remote Similarity	NPD6650	Approved
0.6055	Remote Similarity	NPD6617	Approved
0.6055	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8130	Phase 1
0.6053	Remote Similarity	NPD6059	Approved
0.6053	Remote Similarity	NPD6054	Approved
0.6053	Remote Similarity	NPD6319	Approved
0.6047	Remote Similarity	NPD4747	Approved
0.6047	Remote Similarity	NPD4691	Approved
0.6038	Remote Similarity	NPD4768	Approved
0.6038	Remote Similarity	NPD4767	Approved
0.6034	Remote Similarity	NPD7604	Phase 2
0.6024	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5209	Approved
0.6022	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5785	Approved
0.6019	Remote Similarity	NPD7640	Approved
0.6019	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD8297	Approved
0.6	Remote Similarity	NPD5983	Phase 2
0.598	Remote Similarity	NPD5959	Approved
0.5979	Remote Similarity	NPD4518	Approved
0.5977	Remote Similarity	NPD5276	Approved
0.596	Remote Similarity	NPD5281	Approved
0.596	Remote Similarity	NPD5284	Approved
0.5957	Remote Similarity	NPD4788	Approved
0.5955	Remote Similarity	NPD3703	Phase 2
0.5948	Remote Similarity	NPD6370	Approved
0.5948	Remote Similarity	NPD5988	Approved
0.5941	Remote Similarity	NPD5654	Approved
0.5941	Remote Similarity	NPD5210	Approved
0.5941	Remote Similarity	NPD4629	Approved
0.5938	Remote Similarity	NPD5786	Approved
0.5926	Remote Similarity	NPD5128	Approved
0.5926	Remote Similarity	NPD4730	Approved
0.5926	Remote Similarity	NPD4729	Approved
0.5905	Remote Similarity	NPD7632	Discontinued
0.59	Remote Similarity	NPD5133	Approved
0.5895	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4096	Approved
0.5847	Remote Similarity	NPD7492	Approved
0.5843	Remote Similarity	NPD4058	Approved
0.5843	Remote Similarity	NPD5733	Approved
0.5843	Remote Similarity	NPD4687	Approved
0.5842	Remote Similarity	NPD7748	Approved
0.5841	Remote Similarity	NPD6274	Approved
0.5833	Remote Similarity	NPD5363	Approved
0.5833	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7902	Approved
0.5818	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5250	Approved
0.5818	Remote Similarity	NPD5249	Phase 3
0.5818	Remote Similarity	NPD5169	Approved
0.5818	Remote Similarity	NPD5248	Approved
0.5818	Remote Similarity	NPD5135	Approved
0.5818	Remote Similarity	NPD5247	Approved
0.5818	Remote Similarity	NPD5251	Approved
0.5806	Remote Similarity	NPD4695	Discontinued
0.58	Remote Similarity	NPD7983	Approved
0.58	Remote Similarity	NPD6411	Approved
0.5798	Remote Similarity	NPD6336	Discontinued
0.5798	Remote Similarity	NPD6616	Approved
0.5795	Remote Similarity	NPD5777	Approved
0.5789	Remote Similarity	NPD6695	Phase 3
0.5789	Remote Similarity	NPD6317	Approved
0.5789	Remote Similarity	NPD5362	Discontinued
0.578	Remote Similarity	NPD6686	Approved
0.5773	Remote Similarity	NPD4519	Discontinued
0.5773	Remote Similarity	NPD4623	Approved
0.5773	Remote Similarity	NPD4249	Approved
0.5766	Remote Similarity	NPD5216	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