NPASS Compound

Structure

CID327383 OpenBabel06191716192D 37 37 0 0 1 0 0 0 0 0999 V2000 -20.7846 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.7846 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.9186 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 24 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 24 31 1 6 0 0 0 25 32 1 1 0 0 0 26 33 1 1 0 0 0 27 34 1 1 0 0 0 28 35 1 1 0 0 0 29 23 1 6 0 0 0 29 37 1 0 0 0 0 30 36 2 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.4
Volume:	575.138
LogP:	6.017
LogD:	3.224
LogS:	-6.151
# Rotatable Bonds:	24
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.067
Synthetic Accessibility Score:	4.436
Fsp3:	0.9
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.323
MDCK Permeability:	4.175449430476874e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	95.68370819091797%
Volume Distribution (VD):	1.107
Pgp-substrate:	3.860935688018799%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.172
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.371
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.547
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	10.268
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.639
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.978
Carcinogencity:	0.126
Eye Corrosion:	0.255
Eye Irritation:	0.664
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC327383

Natural Product ID:	NPC327383
*Common Name:**	Cryptocaryols A
IUPAC Name:	(2R)-2-[(2R,4R,6R,8R,10S)-2,4,6,8,10-pentahydroxypentacosyl]-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	GHNAMLOEGLSFMB-ZHMMVFJOSA-N
Standard InCHI:	InChI=1S/C30H56O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-24(31)19-25(32)20-26(33)21-27(34)22-28(35)23-29-17-15-18-30(36)37-29/h15,18,24-29,31-35H,2-14,16-17,19-23H2,1H3/t24-,25+,26+,27+,28+,29+/m0/s1
SMILES:	CCCCCCCCCCCCCCCC(CC(CC(CC(CC(CC1CC=CC(=O)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3287577
PubChem CID:	71761758
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO29906	Cryptocarya	Genus	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539301]

☑ 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	3
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4409	Individual Protein	Programmed cell death protein 4	Homo sapiens	Ratio	=	3.6	n.a.	PMID[531331]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8100.0	nM	PMID[531331]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	4200.0	nM	PMID[531331]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.78	n.a.	PMID[531331]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	1.34	n.a.	PMID[531331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5400.0	nM	PMID[531331]

☑ 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 NPC327383 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	169
0.1-0.2	1701
0.2-0.3	6197
0.3-0.4	16929
0.4-0.5	10808
0.5-0.6	4788
0.6-0.7	1732
0.7-0.8	320
0.8-0.85	26
0.85-0.9	7
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC185186
0.971	High Similarity	NPC285840
0.971	High Similarity	NPC327041
0.942	High Similarity	NPC329914
0.9306	High Similarity	NPC248775
0.9178	High Similarity	NPC139712
0.9178	High Similarity	NPC180725
0.9178	High Similarity	NPC470148
0.9178	High Similarity	NPC470149
0.9167	High Similarity	NPC474026
0.9143	High Similarity	NPC329890
0.913	High Similarity	NPC476012
0.9054	High Similarity	NPC133226
0.9054	High Similarity	NPC470147
0.9028	High Similarity	NPC188860
0.8904	High Similarity	NPC233071
0.8857	High Similarity	NPC476037
0.8732	High Similarity	NPC475762
0.8649	High Similarity	NPC475711
0.8442	Intermediate Similarity	NPC8538
0.8442	Intermediate Similarity	NPC184208
0.8421	Intermediate Similarity	NPC1180
0.831	Intermediate Similarity	NPC475760
0.8286	Intermediate Similarity	NPC146811
0.8209	Intermediate Similarity	NPC22897
0.8209	Intermediate Similarity	NPC159650
0.8205	Intermediate Similarity	NPC315731
0.8205	Intermediate Similarity	NPC469469
0.8158	Intermediate Similarity	NPC477203
0.8148	Intermediate Similarity	NPC208473
0.8143	Intermediate Similarity	NPC96414
0.8108	Intermediate Similarity	NPC477085
0.8072	Intermediate Similarity	NPC133450
0.8049	Intermediate Similarity	NPC199382
0.8028	Intermediate Similarity	NPC201356
0.8026	Intermediate Similarity	NPC477202
0.8026	Intermediate Similarity	NPC469880
0.7976	Intermediate Similarity	NPC3952
0.7976	Intermediate Similarity	NPC177668
0.7973	Intermediate Similarity	NPC477087
0.7973	Intermediate Similarity	NPC477086
0.7971	Intermediate Similarity	NPC26810
0.7949	Intermediate Similarity	NPC473947
0.7901	Intermediate Similarity	NPC160517
0.7901	Intermediate Similarity	NPC186155
0.7901	Intermediate Similarity	NPC78673
0.7901	Intermediate Similarity	NPC474251
0.7901	Intermediate Similarity	NPC473308
0.7895	Intermediate Similarity	NPC260396
0.7882	Intermediate Similarity	NPC114172
0.7882	Intermediate Similarity	NPC471324
0.7882	Intermediate Similarity	NPC476075
0.7882	Intermediate Similarity	NPC476084
0.7882	Intermediate Similarity	NPC206679
0.7875	Intermediate Similarity	NPC251026
0.7831	Intermediate Similarity	NPC316138
0.7831	Intermediate Similarity	NPC313658
0.7826	Intermediate Similarity	NPC26223
0.7805	Intermediate Similarity	NPC471494
0.7791	Intermediate Similarity	NPC109406
0.7791	Intermediate Similarity	NPC159092
0.7778	Intermediate Similarity	NPC142111
0.7778	Intermediate Similarity	NPC473315
0.7746	Intermediate Similarity	NPC25747
0.7746	Intermediate Similarity	NPC148233
0.7746	Intermediate Similarity	NPC308457
0.7733	Intermediate Similarity	NPC293114
0.7733	Intermediate Similarity	NPC316185
0.7722	Intermediate Similarity	NPC226226
0.7722	Intermediate Similarity	NPC55304
0.7711	Intermediate Similarity	NPC47220
0.7711	Intermediate Similarity	NPC47937
0.7711	Intermediate Similarity	NPC186332
0.7711	Intermediate Similarity	NPC61527
0.7703	Intermediate Similarity	NPC475004
0.7703	Intermediate Similarity	NPC151481
0.7703	Intermediate Similarity	NPC101622
0.7701	Intermediate Similarity	NPC256368
0.7692	Intermediate Similarity	NPC84360
0.7639	Intermediate Similarity	NPC282760
0.7639	Intermediate Similarity	NPC19769
0.7632	Intermediate Similarity	NPC284006
0.7606	Intermediate Similarity	NPC29697
0.76	Intermediate Similarity	NPC4299
0.7595	Intermediate Similarity	NPC182292
0.7595	Intermediate Similarity	NPC477314
0.759	Intermediate Similarity	NPC182383
0.759	Intermediate Similarity	NPC471567
0.759	Intermediate Similarity	NPC120398
0.759	Intermediate Similarity	NPC322529
0.7568	Intermediate Similarity	NPC474823
0.7568	Intermediate Similarity	NPC238223
0.7564	Intermediate Similarity	NPC326661
0.7561	Intermediate Similarity	NPC253801
0.7561	Intermediate Similarity	NPC2379
0.7561	Intermediate Similarity	NPC106912
0.7561	Intermediate Similarity	NPC31019
0.7561	Intermediate Similarity	NPC263087
0.7561	Intermediate Similarity	NPC27314
0.7561	Intermediate Similarity	NPC474809
0.7558	Intermediate Similarity	NPC473311
0.7536	Intermediate Similarity	NPC23418
0.7534	Intermediate Similarity	NPC124586
0.7534	Intermediate Similarity	NPC276299
0.7534	Intermediate Similarity	NPC284447
0.7532	Intermediate Similarity	NPC107654
0.7532	Intermediate Similarity	NPC477204
0.7532	Intermediate Similarity	NPC315843
0.7531	Intermediate Similarity	NPC297440
0.7531	Intermediate Similarity	NPC475944
0.7529	Intermediate Similarity	NPC20339
0.7529	Intermediate Similarity	NPC48338
0.7529	Intermediate Similarity	NPC233551
0.7529	Intermediate Similarity	NPC40376
0.7529	Intermediate Similarity	NPC280621
0.7529	Intermediate Similarity	NPC21208
0.75	Intermediate Similarity	NPC142117
0.75	Intermediate Similarity	NPC62118
0.75	Intermediate Similarity	NPC171174
0.75	Intermediate Similarity	NPC114694
0.75	Intermediate Similarity	NPC477456
0.75	Intermediate Similarity	NPC477457
0.75	Intermediate Similarity	NPC477088
0.75	Intermediate Similarity	NPC279267
0.75	Intermediate Similarity	NPC311163
0.75	Intermediate Similarity	NPC69082
0.75	Intermediate Similarity	NPC240695
0.75	Intermediate Similarity	NPC107717
0.75	Intermediate Similarity	NPC232555
0.75	Intermediate Similarity	NPC231096
0.75	Intermediate Similarity	NPC475581
0.75	Intermediate Similarity	NPC309211
0.747	Intermediate Similarity	NPC156804
0.747	Intermediate Similarity	NPC163093
0.747	Intermediate Similarity	NPC266718
0.7467	Intermediate Similarity	NPC470436
0.7465	Intermediate Similarity	NPC325929
0.7465	Intermediate Similarity	NPC271282
0.7465	Intermediate Similarity	NPC66460
0.7444	Intermediate Similarity	NPC475332
0.7439	Intermediate Similarity	NPC131002
0.7439	Intermediate Similarity	NPC473529
0.7439	Intermediate Similarity	NPC475159
0.7439	Intermediate Similarity	NPC329829
0.7439	Intermediate Similarity	NPC94875
0.7439	Intermediate Similarity	NPC145914
0.7439	Intermediate Similarity	NPC65930
0.7439	Intermediate Similarity	NPC11332
0.7439	Intermediate Similarity	NPC180363
0.7439	Intermediate Similarity	NPC73310
0.7439	Intermediate Similarity	NPC473712
0.7439	Intermediate Similarity	NPC473780
0.7432	Intermediate Similarity	NPC122627
0.7432	Intermediate Similarity	NPC132286
0.7429	Intermediate Similarity	NPC97570
0.7429	Intermediate Similarity	NPC474267
0.7416	Intermediate Similarity	NPC300710
0.7412	Intermediate Similarity	NPC178215
0.7412	Intermediate Similarity	NPC473995
0.7403	Intermediate Similarity	NPC470435
0.7386	Intermediate Similarity	NPC472195
0.7386	Intermediate Similarity	NPC238090
0.7386	Intermediate Similarity	NPC472196
0.7381	Intermediate Similarity	NPC82795
0.7381	Intermediate Similarity	NPC103284
0.7381	Intermediate Similarity	NPC66346
0.7381	Intermediate Similarity	NPC1083
0.7381	Intermediate Similarity	NPC477018
0.7381	Intermediate Similarity	NPC39167
0.7381	Intermediate Similarity	NPC67081
0.7381	Intermediate Similarity	NPC471223
0.7381	Intermediate Similarity	NPC473478
0.7381	Intermediate Similarity	NPC473669
0.7381	Intermediate Similarity	NPC283085
0.7381	Intermediate Similarity	NPC25764
0.7381	Intermediate Similarity	NPC110710
0.7381	Intermediate Similarity	NPC477014
0.7381	Intermediate Similarity	NPC242233
0.7381	Intermediate Similarity	NPC100921
0.7381	Intermediate Similarity	NPC9678
0.7381	Intermediate Similarity	NPC286338
0.7381	Intermediate Similarity	NPC470124
0.7381	Intermediate Similarity	NPC292809
0.7381	Intermediate Similarity	NPC107986
0.7381	Intermediate Similarity	NPC477013
0.7381	Intermediate Similarity	NPC329615
0.7381	Intermediate Similarity	NPC473156
0.7381	Intermediate Similarity	NPC470400
0.7381	Intermediate Similarity	NPC39279
0.7381	Intermediate Similarity	NPC235809
0.7381	Intermediate Similarity	NPC223871
0.7381	Intermediate Similarity	NPC77871
0.7381	Intermediate Similarity	NPC319036
0.7381	Intermediate Similarity	NPC132496
0.7381	Intermediate Similarity	NPC202055
0.7381	Intermediate Similarity	NPC231009
0.7381	Intermediate Similarity	NPC473651
0.7381	Intermediate Similarity	NPC473671
0.7381	Intermediate Similarity	NPC475268
0.7381	Intermediate Similarity	NPC329838

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 NPC327383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	2380
0.2-0.3	3811
0.3-0.4	2145
0.4-0.5	536
0.5-0.6	119
0.6-0.7	27
0.7-0.8	2
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
0.7558	Intermediate Similarity	NPD7838	Discovery
0.7356	Intermediate Similarity	NPD6698	Approved
0.7356	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5344	Discontinued
0.6989	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4251	Approved
0.6818	Remote Similarity	NPD4250	Approved
0.6786	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6648	Approved
0.6711	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4249	Approved
0.6593	Remote Similarity	NPD5785	Approved
0.6579	Remote Similarity	NPD3197	Phase 1
0.6552	Remote Similarity	NPD7154	Phase 3
0.6548	Remote Similarity	NPD4268	Approved
0.6548	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD7983	Approved
0.6458	Remote Similarity	NPD7638	Approved
0.6452	Remote Similarity	NPD5778	Approved
0.6452	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD4756	Discovery
0.6404	Remote Similarity	NPD5363	Approved
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6392	Remote Similarity	NPD7639	Approved
0.6392	Remote Similarity	NPD7640	Approved
0.6344	Remote Similarity	NPD7637	Suspended
0.6289	Remote Similarity	NPD4225	Approved
0.6275	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD4266	Approved
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6053	Discontinued
0.618	Remote Similarity	NPD5362	Discontinued
0.6176	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6371	Approved
0.6146	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6109	Phase 1
0.6111	Remote Similarity	NPD3172	Approved
0.6095	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6435	Approved
0.6067	Remote Similarity	NPD4270	Approved
0.6067	Remote Similarity	NPD4269	Approved
0.6067	Remote Similarity	NPD5209	Approved
0.6056	Remote Similarity	NPD6927	Phase 3
0.6044	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD5332	Approved
0.6	Remote Similarity	NPD8039	Approved
0.5978	Remote Similarity	NPD5786	Approved
0.5977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6101	Approved
0.5957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4790	Discontinued
0.5955	Remote Similarity	NPD5369	Approved
0.5949	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4211	Phase 1
0.5921	Remote Similarity	NPD69	Approved
0.5921	Remote Similarity	NPD9119	Approved
0.5895	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7503	Approved
0.5889	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD5343	Approved
0.5843	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD29	Approved
0.5833	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD28	Approved
0.5824	Remote Similarity	NPD6695	Phase 3
0.5824	Remote Similarity	NPD6110	Phase 1
0.5823	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7115	Discovery
0.5802	Remote Similarity	NPD3704	Approved
0.5802	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD39	Approved
0.5789	Remote Similarity	NPD9118	Approved
0.5789	Remote Similarity	NPD1695	Approved
0.5789	Remote Similarity	NPD7830	Approved
0.5789	Remote Similarity	NPD7829	Approved
0.5789	Remote Similarity	NPD5370	Suspended
0.5784	Remote Similarity	NPD7632	Discontinued
0.5775	Remote Similarity	NPD3173	Approved
0.5765	Remote Similarity	NPD4732	Discontinued
0.5761	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5282	Discontinued
0.5699	Remote Similarity	NPD1694	Approved
0.5667	Remote Similarity	NPD7332	Phase 2
0.5667	Remote Similarity	NPD7514	Phase 3
0.5652	Remote Similarity	NPD7642	Approved
0.5652	Remote Similarity	NPD6097	Approved
0.5652	Remote Similarity	NPD6096	Approved
0.5625	Remote Similarity	NPD7327	Approved
0.5625	Remote Similarity	NPD7328	Approved
0.5625	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7145	Approved
0.5614	Remote Similarity	NPD8513	Phase 3
0.5614	Remote Similarity	NPD8033	Approved
0.5604	Remote Similarity	NPD6902	Approved
0.56	Remote Similarity	NPD3730	Approved
0.56	Remote Similarity	NPD3728	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