NPASS Compound

Structure

CID20262 OpenBabel06191715342D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.9453 -3.1751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2980 -3.7103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6310 -2.0898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7093 -0.7731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2459 -1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 -0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 0.7346 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 -2.9672 -2.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -1.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4540 0.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 -2.0161 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7071 -1.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5981 -0.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7071 -0.7071 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 2.4891 -0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6589 -0.7522 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 4 14 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 13 3 1 1 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 12 1 1 0 0 0 15 16 1 0 0 0 0 16 19 1 1 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 6 0 0 0 19 5 1 1 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	4.568
LogD:	4.403
LogS:	-4.778
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	4.667
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:	-4.675
MDCK Permeability:	2.2715898012393154e-05
Pgp-inhibitor:	0.559
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.77
Plasma Protein Binding (PPB):	95.25464630126953%
Volume Distribution (VD):	1.017
Pgp-substrate:	3.5777430534362793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.471
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.481
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.716

ADMET: Excretion

Clearance (CL):	10.312
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.511
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.926
Carcinogencity:	0.505
Eye Corrosion:	0.906
Eye Irritation:	0.784
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC20262

Natural Product ID:	NPC20262
*Common Name:**	DJXIIUFLBYBOFZ-IKSQAYNDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DJXIIUFLBYBOFZ-IKSQAYNDSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-12(2)15-8-9-19(5)11-20(22)14(4)10-17(21)18(20)13(3)6-7-16(15)19/h10,12-13,15-16,18,22H,6-9,11H2,1-5H3/t13-,15+,16-,18-,19+,20+/m0/s1
SMILES:	CC(C)[C@H]1CC[C@]2(C)C[C@]3(C(=CC(=O)[C@@H]3[C@@H](C)CC[C@@H]12)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774427
PubChem CID:	52951743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003547] Fusicoccane 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
NPO30691	Porella chilensis	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[21384863]
NPO30691	Porella chilensis	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21384863]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	15.0	%	PMID[526227]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	95.0	%	PMID[526227]

☑ 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 NPC20262 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	178
0.1-0.2	1541
0.2-0.3	7840
0.3-0.4	16176
0.4-0.5	8650
0.5-0.6	6164
0.6-0.7	1913
0.7-0.8	223
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC256750
0.9605	High Similarity	NPC32758
0.9351	High Similarity	NPC301769
0.8488	Intermediate Similarity	NPC170775
0.8462	Intermediate Similarity	NPC7382
0.8354	Intermediate Similarity	NPC251435
0.8354	Intermediate Similarity	NPC77501
0.825	Intermediate Similarity	NPC182848
0.8228	Intermediate Similarity	NPC206875
0.8202	Intermediate Similarity	NPC37816
0.8161	Intermediate Similarity	NPC472677
0.8161	Intermediate Similarity	NPC58532
0.8125	Intermediate Similarity	NPC89374
0.8072	Intermediate Similarity	NPC138492
0.8072	Intermediate Similarity	NPC233352
0.8072	Intermediate Similarity	NPC824
0.8068	Intermediate Similarity	NPC41217
0.8023	Intermediate Similarity	NPC179006
0.8023	Intermediate Similarity	NPC474853
0.8	Intermediate Similarity	NPC65350
0.7978	Intermediate Similarity	NPC2946
0.7952	Intermediate Similarity	NPC476624
0.7952	Intermediate Similarity	NPC472013
0.7895	Intermediate Similarity	NPC25639
0.7865	Intermediate Similarity	NPC476388
0.7865	Intermediate Similarity	NPC477215
0.7857	Intermediate Similarity	NPC45495
0.7857	Intermediate Similarity	NPC164218
0.7831	Intermediate Similarity	NPC476627
0.7816	Intermediate Similarity	NPC476628
0.7805	Intermediate Similarity	NPC469646
0.7753	Intermediate Similarity	NPC474854
0.7738	Intermediate Similarity	NPC471890
0.7738	Intermediate Similarity	NPC66677
0.7738	Intermediate Similarity	NPC84185
0.7738	Intermediate Similarity	NPC7232
0.7727	Intermediate Similarity	NPC472869
0.7727	Intermediate Similarity	NPC476043
0.7711	Intermediate Similarity	NPC86917
0.7692	Intermediate Similarity	NPC278895
0.7683	Intermediate Similarity	NPC474011
0.7683	Intermediate Similarity	NPC201263
0.7674	Intermediate Similarity	NPC477269
0.7674	Intermediate Similarity	NPC477270
0.7674	Intermediate Similarity	NPC193347
0.7674	Intermediate Similarity	NPC129080
0.7674	Intermediate Similarity	NPC477271
0.7674	Intermediate Similarity	NPC133844
0.7654	Intermediate Similarity	NPC300940
0.764	Intermediate Similarity	NPC136948
0.7619	Intermediate Similarity	NPC275494
0.7619	Intermediate Similarity	NPC471409
0.7604	Intermediate Similarity	NPC195192
0.7604	Intermediate Similarity	NPC304738
0.759	Intermediate Similarity	NPC215481
0.7586	Intermediate Similarity	NPC477373
0.7582	Intermediate Similarity	NPC306168
0.7582	Intermediate Similarity	NPC49946
0.7558	Intermediate Similarity	NPC477372
0.7558	Intermediate Similarity	NPC171665
0.7556	Intermediate Similarity	NPC117122
0.7556	Intermediate Similarity	NPC477710
0.7556	Intermediate Similarity	NPC472870
0.7531	Intermediate Similarity	NPC469737
0.7529	Intermediate Similarity	NPC215843
0.7528	Intermediate Similarity	NPC194417
0.75	Intermediate Similarity	NPC472864
0.75	Intermediate Similarity	NPC469677
0.75	Intermediate Similarity	NPC19849
0.75	Intermediate Similarity	NPC475806
0.75	Intermediate Similarity	NPC210346
0.75	Intermediate Similarity	NPC164577
0.75	Intermediate Similarity	NPC144258
0.75	Intermediate Similarity	NPC472865
0.7474	Intermediate Similarity	NPC477949
0.7473	Intermediate Similarity	NPC232747
0.7473	Intermediate Similarity	NPC473999
0.7473	Intermediate Similarity	NPC472970
0.7473	Intermediate Similarity	NPC262043
0.7473	Intermediate Similarity	NPC472971
0.7473	Intermediate Similarity	NPC309603
0.7473	Intermediate Similarity	NPC2983
0.7473	Intermediate Similarity	NPC123912
0.747	Intermediate Similarity	NPC469669
0.747	Intermediate Similarity	NPC475771
0.747	Intermediate Similarity	NPC469678
0.7447	Intermediate Similarity	NPC476488
0.7447	Intermediate Similarity	NPC476487
0.7444	Intermediate Similarity	NPC287079
0.7442	Intermediate Similarity	NPC279667
0.7442	Intermediate Similarity	NPC74445
0.7442	Intermediate Similarity	NPC287817
0.7416	Intermediate Similarity	NPC471224
0.7416	Intermediate Similarity	NPC269638
0.7416	Intermediate Similarity	NPC474083
0.7403	Intermediate Similarity	NPC474480
0.7391	Intermediate Similarity	NPC48010
0.7391	Intermediate Similarity	NPC477711
0.7391	Intermediate Similarity	NPC472866
0.7386	Intermediate Similarity	NPC310470
0.7386	Intermediate Similarity	NPC97913
0.7381	Intermediate Similarity	NPC142759
0.7381	Intermediate Similarity	NPC25908
0.7381	Intermediate Similarity	NPC141346
0.7381	Intermediate Similarity	NPC115719
0.7381	Intermediate Similarity	NPC473437
0.7381	Intermediate Similarity	NPC124289
0.7375	Intermediate Similarity	NPC469679
0.7375	Intermediate Similarity	NPC469688
0.7368	Intermediate Similarity	NPC29152
0.7368	Intermediate Similarity	NPC9812
0.7356	Intermediate Similarity	NPC78677
0.7356	Intermediate Similarity	NPC47031
0.7356	Intermediate Similarity	NPC59994
0.7349	Intermediate Similarity	NPC167049
0.7349	Intermediate Similarity	NPC469691
0.734	Intermediate Similarity	NPC90453
0.734	Intermediate Similarity	NPC53685
0.734	Intermediate Similarity	NPC8993
0.734	Intermediate Similarity	NPC298919
0.7333	Intermediate Similarity	NPC469994
0.7333	Intermediate Similarity	NPC472479
0.7333	Intermediate Similarity	NPC186975
0.7326	Intermediate Similarity	NPC477371
0.7317	Intermediate Similarity	NPC29328
0.7317	Intermediate Similarity	NPC144627
0.7317	Intermediate Similarity	NPC471660
0.7317	Intermediate Similarity	NPC106309
0.7312	Intermediate Similarity	NPC144629
0.7312	Intermediate Similarity	NPC473998
0.7312	Intermediate Similarity	NPC204341
0.7303	Intermediate Similarity	NPC214043
0.7303	Intermediate Similarity	NPC85774
0.7303	Intermediate Similarity	NPC473246
0.7303	Intermediate Similarity	NPC90446
0.7303	Intermediate Similarity	NPC238197
0.7303	Intermediate Similarity	NPC472480
0.7303	Intermediate Similarity	NPC230527
0.7303	Intermediate Similarity	NPC7927
0.7303	Intermediate Similarity	NPC476412
0.7294	Intermediate Similarity	NPC276769
0.7294	Intermediate Similarity	NPC266193
0.7294	Intermediate Similarity	NPC257666
0.7294	Intermediate Similarity	NPC472014
0.7294	Intermediate Similarity	NPC266124
0.7292	Intermediate Similarity	NPC156546
0.7284	Intermediate Similarity	NPC469914
0.7283	Intermediate Similarity	NPC214387
0.7273	Intermediate Similarity	NPC469325
0.7273	Intermediate Similarity	NPC7414
0.7273	Intermediate Similarity	NPC320514
0.7263	Intermediate Similarity	NPC259286
0.7263	Intermediate Similarity	NPC472932
0.7263	Intermediate Similarity	NPC271195
0.7253	Intermediate Similarity	NPC236618
0.7253	Intermediate Similarity	NPC128644
0.7245	Intermediate Similarity	NPC475099
0.7245	Intermediate Similarity	NPC206079
0.7245	Intermediate Similarity	NPC477950
0.7237	Intermediate Similarity	NPC259261
0.7237	Intermediate Similarity	NPC5698
0.7234	Intermediate Similarity	NPC477520
0.7234	Intermediate Similarity	NPC474736
0.7234	Intermediate Similarity	NPC472871
0.7234	Intermediate Similarity	NPC474807
0.7234	Intermediate Similarity	NPC69454
0.7234	Intermediate Similarity	NPC125180
0.7234	Intermediate Similarity	NPC472930
0.7229	Intermediate Similarity	NPC107783
0.7229	Intermediate Similarity	NPC247586
0.7229	Intermediate Similarity	NPC92909
0.7229	Intermediate Similarity	NPC275098
0.7222	Intermediate Similarity	NPC125290
0.7222	Intermediate Similarity	NPC29447
0.7222	Intermediate Similarity	NPC469948
0.7222	Intermediate Similarity	NPC245434
0.7216	Intermediate Similarity	NPC471610
0.7216	Intermediate Similarity	NPC64742
0.7216	Intermediate Similarity	NPC244411
0.7209	Intermediate Similarity	NPC475994
0.7209	Intermediate Similarity	NPC169095
0.7209	Intermediate Similarity	NPC297996
0.7209	Intermediate Similarity	NPC192006
0.7204	Intermediate Similarity	NPC69622
0.7204	Intermediate Similarity	NPC126993
0.7204	Intermediate Similarity	NPC320026
0.7204	Intermediate Similarity	NPC477149
0.7204	Intermediate Similarity	NPC477147
0.7195	Intermediate Similarity	NPC203819
0.7195	Intermediate Similarity	NPC18543
0.7191	Intermediate Similarity	NPC62214
0.7191	Intermediate Similarity	NPC474748
0.7188	Intermediate Similarity	NPC249954
0.7176	Intermediate Similarity	NPC472305
0.7176	Intermediate Similarity	NPC263582
0.7176	Intermediate Similarity	NPC310643
0.7176	Intermediate Similarity	NPC279537
0.7174	Intermediate Similarity	NPC320665
0.7174	Intermediate Similarity	NPC328313
0.7174	Intermediate Similarity	NPC72397

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 NPC20262 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	2240
0.2-0.3	4253
0.3-0.4	1763
0.4-0.5	362
0.5-0.6	247
0.6-0.7	98
0.7-0.8	8
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
0.7674	Intermediate Similarity	NPD4221	Approved
0.7674	Intermediate Similarity	NPD4223	Phase 3
0.7614	Intermediate Similarity	NPD5329	Approved
0.75	Intermediate Similarity	NPD4197	Approved
0.7416	Intermediate Similarity	NPD5363	Approved
0.7412	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5785	Approved
0.7386	Intermediate Similarity	NPD5362	Discontinued
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4693	Phase 3
0.7333	Intermediate Similarity	NPD4519	Discontinued
0.7333	Intermediate Similarity	NPD5690	Phase 2
0.7333	Intermediate Similarity	NPD4694	Approved
0.7333	Intermediate Similarity	NPD4689	Approved
0.7333	Intermediate Similarity	NPD4623	Approved
0.7333	Intermediate Similarity	NPD4138	Approved
0.7333	Intermediate Similarity	NPD5280	Approved
0.7333	Intermediate Similarity	NPD5205	Approved
0.7333	Intermediate Similarity	NPD4690	Approved
0.7333	Intermediate Similarity	NPD4688	Approved
0.7273	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4270	Approved
0.7273	Intermediate Similarity	NPD4269	Approved
0.7174	Intermediate Similarity	NPD4518	Approved
0.7125	Intermediate Similarity	NPD7331	Phase 2
0.7111	Intermediate Similarity	NPD3133	Approved
0.7111	Intermediate Similarity	NPD3665	Phase 1
0.7111	Intermediate Similarity	NPD3666	Approved
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7045	Intermediate Similarity	NPD4252	Approved
0.7021	Intermediate Similarity	NPD4096	Approved
0.7	Intermediate Similarity	NPD7341	Phase 2
0.6966	Remote Similarity	NPD5369	Approved
0.6957	Remote Similarity	NPD5279	Phase 3
0.6957	Remote Similarity	NPD5786	Approved
0.6947	Remote Similarity	NPD5281	Approved
0.6947	Remote Similarity	NPD5284	Approved
0.6932	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD4786	Approved
0.6915	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD4202	Approved
0.6818	Remote Similarity	NPD3617	Approved
0.6813	Remote Similarity	NPD5331	Approved
0.6813	Remote Similarity	NPD5332	Approved
0.6813	Remote Similarity	NPD4788	Approved
0.6804	Remote Similarity	NPD5282	Discontinued
0.6778	Remote Similarity	NPD4790	Discontinued
0.6778	Remote Similarity	NPD4139	Approved
0.6778	Remote Similarity	NPD4692	Approved
0.6774	Remote Similarity	NPD3618	Phase 1
0.6771	Remote Similarity	NPD6079	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6737	Remote Similarity	NPD6904	Approved
0.6737	Remote Similarity	NPD6080	Approved
0.6737	Remote Similarity	NPD6673	Approved
0.6735	Remote Similarity	NPD5695	Phase 3
0.6735	Remote Similarity	NPD4629	Approved
0.6735	Remote Similarity	NPD5210	Approved
0.6703	Remote Similarity	NPD3667	Approved
0.6701	Remote Similarity	NPD5133	Approved
0.6698	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD4822	Approved
0.6632	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD6903	Approved
0.66	Remote Similarity	NPD4755	Approved
0.6598	Remote Similarity	NPD6050	Approved
0.6598	Remote Similarity	NPD5693	Phase 1
0.6596	Remote Similarity	NPD7334	Approved
0.6596	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD5330	Approved
0.6596	Remote Similarity	NPD6098	Approved
0.6596	Remote Similarity	NPD7146	Approved
0.6596	Remote Similarity	NPD6684	Approved
0.6596	Remote Similarity	NPD7521	Approved
0.6588	Remote Similarity	NPD4747	Approved
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5733	Approved
0.6538	Remote Similarity	NPD5141	Approved
0.6535	Remote Similarity	NPD5696	Approved
0.6512	Remote Similarity	NPD4243	Approved
0.6512	Remote Similarity	NPD5276	Approved
0.6495	Remote Similarity	NPD5692	Phase 3
0.6484	Remote Similarity	NPD5368	Approved
0.6471	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4137	Phase 3
0.6471	Remote Similarity	NPD4696	Approved
0.6471	Remote Similarity	NPD6404	Discontinued
0.6471	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD6001	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6458	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5737	Approved
0.6452	Remote Similarity	NPD7154	Phase 3
0.6444	Remote Similarity	NPD4268	Approved
0.6444	Remote Similarity	NPD4271	Approved
0.6429	Remote Similarity	NPD5694	Approved
0.6415	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5223	Approved
0.6395	Remote Similarity	NPD4691	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD4785	Approved
0.6364	Remote Similarity	NPD4687	Approved
0.6364	Remote Similarity	NPD6926	Approved
0.6364	Remote Similarity	NPD4784	Approved
0.6364	Remote Similarity	NPD6924	Approved
0.6355	Remote Similarity	NPD7320	Approved
0.6346	Remote Similarity	NPD5224	Approved
0.6346	Remote Similarity	NPD5091	Approved
0.6346	Remote Similarity	NPD5225	Approved
0.6346	Remote Similarity	NPD5226	Approved
0.6346	Remote Similarity	NPD4633	Approved
0.6344	Remote Similarity	NPD6435	Approved
0.6344	Remote Similarity	NPD5209	Approved
0.6339	Remote Similarity	NPD7115	Discovery
0.6337	Remote Similarity	NPD4697	Phase 3
0.6337	Remote Similarity	NPD5221	Approved
0.6337	Remote Similarity	NPD5222	Approved
0.6337	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1696	Phase 3
0.6304	Remote Similarity	NPD6930	Phase 2
0.6304	Remote Similarity	NPD6931	Approved
0.6304	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD5175	Approved
0.6286	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5173	Approved
0.6264	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7637	Suspended
0.6239	Remote Similarity	NPD4634	Approved
0.6237	Remote Similarity	NPD857	Phase 3
0.6222	Remote Similarity	NPD6933	Approved
0.6211	Remote Similarity	NPD3668	Phase 3
0.6204	Remote Similarity	NPD6881	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6196	Remote Similarity	NPD6929	Approved
0.618	Remote Similarity	NPD4058	Approved
0.617	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4767	Approved
0.6168	Remote Similarity	NPD4768	Approved
0.6154	Remote Similarity	NPD7639	Approved
0.6154	Remote Similarity	NPD7640	Approved
0.6147	Remote Similarity	NPD6373	Approved
0.6147	Remote Similarity	NPD6372	Approved
0.6132	Remote Similarity	NPD6052	Approved
0.6129	Remote Similarity	NPD7332	Phase 2
0.6129	Remote Similarity	NPD7514	Phase 3
0.6111	Remote Similarity	NPD5697	Approved
0.6111	Remote Similarity	NPD4190	Phase 3
0.6111	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD5275	Approved
0.6105	Remote Similarity	NPD6695	Phase 3
0.61	Remote Similarity	NPD7515	Phase 2
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6078	Remote Similarity	NPD5654	Approved
0.6061	Remote Similarity	NPD5370	Suspended
0.6061	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7638	Approved
0.6055	Remote Similarity	NPD4730	Approved
0.6055	Remote Similarity	NPD4729	Approved
0.6055	Remote Similarity	NPD5128	Approved
0.6055	Remote Similarity	NPD6011	Approved
0.6042	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5778	Approved
0.604	Remote Similarity	NPD5779	Approved
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6869	Approved
0.6036	Remote Similarity	NPD6649	Approved
0.6034	Remote Similarity	NPD6059	Approved
0.6034	Remote Similarity	NPD6054	Approved
0.602	Remote Similarity	NPD4251	Approved
0.602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6053	Discontinued
0.5982	Remote Similarity	NPD8297	Approved
0.5982	Remote Similarity	NPD6882	Approved
0.598	Remote Similarity	NPD7748	Approved
0.5979	Remote Similarity	NPD7520	Clinical (unspecified phase)

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