NPASS Compound

Structure

NPC1761 OpenBabel07101718322D 26 26 0 0 1 0 0 0 0 0999 V2000 -3.4115 -0.6015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5248 0.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4333 0.0977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5924 -1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 2.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8794 0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8191 1.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7057 -0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -0.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 2.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3420 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5851 0.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 -0.6428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8420 1.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3420 0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5924 3.5070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 0.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6924 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8420 1.8057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 11 19 2 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 23 2 0 0 0 0 14 26 1 0 0 0 0 17 4 1 1 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 20 14 1 1 0 0 0 20 22 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 6 0 0 0 22 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.25
Volume:	402.49
LogP:	4.277
LogD:	4.082
LogS:	-4.196
# Rotatable Bonds:	8
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.991
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.588
MDCK Permeability:	8.847338176565245e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.435
Human Intestinal Absorption (HIA):	0.932
20% Bioavailability (F20%):	0.305
30% Bioavailability (F30%):	0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	93.86662292480469%
Volume Distribution (VD):	1.247
Pgp-substrate:	9.889808654785156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.34
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.215
CYP2C19-substrate:	0.531
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.161
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	6.553
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.877
Drug-inuced Liver Injury (DILI):	0.129
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.661
Skin Sensitization:	0.954
Carcinogencity:	0.208
Eye Corrosion:	0.644
Eye Irritation:	0.423
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC1761

Natural Product ID:	NPC1761
*Common Name:**	Hydroxyacetyldictyolal
IUPAC Name:	[(1R,2E,5E,8S,9R)-2-formyl-8-hydroxy-6-methyl-9-[(2S)-6-methylhept-5-en-2-yl]cyclonona-2,5-dien-1-yl]methyl acetate
Synonyms:	Hydroxyacetyldictyolal
Standard InCHIKey:	SYFAUKOFHTVEDD-ZWLOZJGOSA-N
Standard InCHI:	InChI=1S/C22H34O4/c1-15(2)8-6-10-17(4)22-20(14-26-18(5)24)19(13-23)11-7-9-16(3)12-21(22)25/h8-9,11,13,17,20-22,25H,6-7,10,12,14H2,1-5H3/b16-9+,19-11-/t17-,20-,21-,22+/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@@H]1[C@@H](COC(=O)C)/C(=CC/C=C(C)/C[C@@H]1O)/C=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476285
PubChem CID:	23426744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters

*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
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277314]
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[469591]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.9	ug ml-1	PMID[469591]
NPT168	Cell Line	P388	Mus musculus	ED50	=	9.3	ug ml-1	PMID[469591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	10.0	ug ml-1	PMID[469591]

☑ 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 NPC1761 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	198
0.1-0.2	1327
0.2-0.3	5802
0.3-0.4	13347
0.4-0.5	11080
0.5-0.6	6995
0.6-0.7	3466
0.7-0.8	477
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52609
0.8718	High Similarity	NPC472256
0.8256	Intermediate Similarity	NPC150755
0.8148	Intermediate Similarity	NPC472959
0.8025	Intermediate Similarity	NPC324762
0.8023	Intermediate Similarity	NPC474776
0.8	Intermediate Similarity	NPC219874
0.7976	Intermediate Similarity	NPC103634
0.7927	Intermediate Similarity	NPC61863
0.7907	Intermediate Similarity	NPC59097
0.7865	Intermediate Similarity	NPC476704
0.7865	Intermediate Similarity	NPC202672
0.7841	Intermediate Similarity	NPC475461
0.7841	Intermediate Similarity	NPC305475
0.7816	Intermediate Similarity	NPC165287
0.7816	Intermediate Similarity	NPC472958
0.7816	Intermediate Similarity	NPC472957
0.7816	Intermediate Similarity	NPC476804
0.7816	Intermediate Similarity	NPC9868
0.7802	Intermediate Similarity	NPC184463
0.7802	Intermediate Similarity	NPC30515
0.7778	Intermediate Similarity	NPC307411
0.7778	Intermediate Similarity	NPC295312
0.7778	Intermediate Similarity	NPC212598
0.7766	Intermediate Similarity	NPC87090
0.7753	Intermediate Similarity	NPC237540
0.7753	Intermediate Similarity	NPC471738
0.7738	Intermediate Similarity	NPC472960
0.7738	Intermediate Similarity	NPC93763
0.7738	Intermediate Similarity	NPC108816
0.7738	Intermediate Similarity	NPC192006
0.7727	Intermediate Similarity	NPC28887
0.7727	Intermediate Similarity	NPC255307
0.7717	Intermediate Similarity	NPC476049
0.7711	Intermediate Similarity	NPC12740
0.7711	Intermediate Similarity	NPC110461
0.7701	Intermediate Similarity	NPC40746
0.7701	Intermediate Similarity	NPC11620
0.7701	Intermediate Similarity	NPC169575
0.7692	Intermediate Similarity	NPC51004
0.7683	Intermediate Similarity	NPC472966
0.7674	Intermediate Similarity	NPC471325
0.7674	Intermediate Similarity	NPC286229
0.7667	Intermediate Similarity	NPC476805
0.7667	Intermediate Similarity	NPC473229
0.766	Intermediate Similarity	NPC471039
0.7647	Intermediate Similarity	NPC470244
0.7647	Intermediate Similarity	NPC470239
0.7647	Intermediate Similarity	NPC136033
0.764	Intermediate Similarity	NPC164393
0.764	Intermediate Similarity	NPC234038
0.764	Intermediate Similarity	NPC469483
0.7625	Intermediate Similarity	NPC261398
0.7619	Intermediate Similarity	NPC7563
0.7619	Intermediate Similarity	NPC116177
0.7619	Intermediate Similarity	NPC320630
0.7619	Intermediate Similarity	NPC107668
0.7614	Intermediate Similarity	NPC96259
0.7614	Intermediate Similarity	NPC191476
0.7614	Intermediate Similarity	NPC196487
0.7614	Intermediate Similarity	NPC141193
0.7614	Intermediate Similarity	NPC82297
0.7614	Intermediate Similarity	NPC243618
0.7614	Intermediate Similarity	NPC70424
0.7614	Intermediate Similarity	NPC14575
0.7614	Intermediate Similarity	NPC114979
0.7609	Intermediate Similarity	NPC12172
0.7609	Intermediate Similarity	NPC208886
0.7586	Intermediate Similarity	NPC89555
0.7582	Intermediate Similarity	NPC52198
0.7582	Intermediate Similarity	NPC474032
0.7582	Intermediate Similarity	NPC268298
0.7582	Intermediate Similarity	NPC83423
0.7582	Intermediate Similarity	NPC117405
0.7579	Intermediate Similarity	NPC169205
0.7558	Intermediate Similarity	NPC233377
0.7558	Intermediate Similarity	NPC281132
0.7558	Intermediate Similarity	NPC304795
0.7556	Intermediate Similarity	NPC248602
0.7556	Intermediate Similarity	NPC474765
0.7553	Intermediate Similarity	NPC193645
0.7553	Intermediate Similarity	NPC36954
0.7553	Intermediate Similarity	NPC90121
0.7553	Intermediate Similarity	NPC48803
0.7553	Intermediate Similarity	NPC275960
0.7553	Intermediate Similarity	NPC477922
0.7531	Intermediate Similarity	NPC472955
0.7531	Intermediate Similarity	NPC318766
0.7529	Intermediate Similarity	NPC128276
0.7528	Intermediate Similarity	NPC165162
0.7528	Intermediate Similarity	NPC470755
0.7528	Intermediate Similarity	NPC21469
0.7528	Intermediate Similarity	NPC329738
0.7528	Intermediate Similarity	NPC137033
0.7527	Intermediate Similarity	NPC273579
0.7527	Intermediate Similarity	NPC81419
0.7527	Intermediate Similarity	NPC475912
0.7527	Intermediate Similarity	NPC288240
0.7527	Intermediate Similarity	NPC162205
0.7527	Intermediate Similarity	NPC476300
0.7527	Intermediate Similarity	NPC109414
0.7527	Intermediate Similarity	NPC212486
0.7527	Intermediate Similarity	NPC295204
0.7527	Intermediate Similarity	NPC179746
0.7526	Intermediate Similarity	NPC477356
0.75	Intermediate Similarity	NPC129419
0.75	Intermediate Similarity	NPC469368
0.75	Intermediate Similarity	NPC53867
0.75	Intermediate Similarity	NPC473619
0.75	Intermediate Similarity	NPC166554
0.75	Intermediate Similarity	NPC476004
0.75	Intermediate Similarity	NPC474761
0.75	Intermediate Similarity	NPC265856
0.75	Intermediate Similarity	NPC474527
0.75	Intermediate Similarity	NPC473390
0.75	Intermediate Similarity	NPC141191
0.75	Intermediate Similarity	NPC471726
0.75	Intermediate Similarity	NPC473448
0.75	Intermediate Similarity	NPC477355
0.75	Intermediate Similarity	NPC131669
0.7474	Intermediate Similarity	NPC185553
0.7474	Intermediate Similarity	NPC476315
0.7474	Intermediate Similarity	NPC477921
0.7473	Intermediate Similarity	NPC227379
0.7473	Intermediate Similarity	NPC474471
0.7473	Intermediate Similarity	NPC476803
0.7471	Intermediate Similarity	NPC470241
0.7471	Intermediate Similarity	NPC325031
0.7471	Intermediate Similarity	NPC90055
0.7471	Intermediate Similarity	NPC52861
0.7471	Intermediate Similarity	NPC24417
0.7471	Intermediate Similarity	NPC255580
0.7471	Intermediate Similarity	NPC39411
0.747	Intermediate Similarity	NPC476355
0.747	Intermediate Similarity	NPC140287
0.7449	Intermediate Similarity	NPC118405
0.7447	Intermediate Similarity	NPC71589
0.7447	Intermediate Similarity	NPC81386
0.7447	Intermediate Similarity	NPC474035
0.7447	Intermediate Similarity	NPC471040
0.7444	Intermediate Similarity	NPC284902
0.7444	Intermediate Similarity	NPC122502
0.7444	Intermediate Similarity	NPC112685
0.7444	Intermediate Similarity	NPC261721
0.7444	Intermediate Similarity	NPC116575
0.7442	Intermediate Similarity	NPC469620
0.7442	Intermediate Similarity	NPC261125
0.7442	Intermediate Similarity	NPC469690
0.7442	Intermediate Similarity	NPC471740
0.7442	Intermediate Similarity	NPC164308
0.7442	Intermediate Similarity	NPC178277
0.7442	Intermediate Similarity	NPC167881
0.7442	Intermediate Similarity	NPC181195
0.7442	Intermediate Similarity	NPC98557
0.7442	Intermediate Similarity	NPC19841
0.7423	Intermediate Similarity	NPC476274
0.7419	Intermediate Similarity	NPC473321
0.7419	Intermediate Similarity	NPC261607
0.7419	Intermediate Similarity	NPC300312
0.7419	Intermediate Similarity	NPC471059
0.7419	Intermediate Similarity	NPC470379
0.7419	Intermediate Similarity	NPC111114
0.7419	Intermediate Similarity	NPC470373
0.7416	Intermediate Similarity	NPC72464
0.7416	Intermediate Similarity	NPC158756
0.7416	Intermediate Similarity	NPC472326
0.7412	Intermediate Similarity	NPC211279
0.7412	Intermediate Similarity	NPC476794
0.7412	Intermediate Similarity	NPC57744
0.7412	Intermediate Similarity	NPC97516
0.7412	Intermediate Similarity	NPC470240
0.7412	Intermediate Similarity	NPC276769
0.7407	Intermediate Similarity	NPC250928
0.7407	Intermediate Similarity	NPC101622
0.7407	Intermediate Similarity	NPC10758
0.7396	Intermediate Similarity	NPC474343
0.7391	Intermediate Similarity	NPC118193
0.7391	Intermediate Similarity	NPC106040
0.7391	Intermediate Similarity	NPC115179
0.7391	Intermediate Similarity	NPC256902
0.7391	Intermediate Similarity	NPC97577
0.7386	Intermediate Similarity	NPC229825
0.7386	Intermediate Similarity	NPC173609
0.7386	Intermediate Similarity	NPC474291
0.7386	Intermediate Similarity	NPC35556
0.7381	Intermediate Similarity	NPC244166
0.7381	Intermediate Similarity	NPC475861
0.7374	Intermediate Similarity	NPC95585
0.7374	Intermediate Similarity	NPC282233
0.7368	Intermediate Similarity	NPC14961
0.7368	Intermediate Similarity	NPC304886
0.7368	Intermediate Similarity	NPC272050
0.7368	Intermediate Similarity	NPC279313
0.7368	Intermediate Similarity	NPC270013
0.7363	Intermediate Similarity	NPC477959
0.7363	Intermediate Similarity	NPC179659
0.7363	Intermediate Similarity	NPC86005
0.7356	Intermediate Similarity	NPC51507
0.7356	Intermediate Similarity	NPC223904
0.7356	Intermediate Similarity	NPC200446

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 NPC1761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	2015
0.2-0.3	3773
0.3-0.4	2118
0.4-0.5	656
0.5-0.6	293
0.6-0.7	86
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7791	Intermediate Similarity	NPD6435	Approved
0.7558	Intermediate Similarity	NPD5368	Approved
0.7553	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5363	Approved
0.7471	Intermediate Similarity	NPD5369	Approved
0.7444	Intermediate Similarity	NPD5786	Approved
0.7391	Intermediate Similarity	NPD6101	Approved
0.7391	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5785	Approved
0.7312	Intermediate Similarity	NPD46	Approved
0.7312	Intermediate Similarity	NPD6698	Approved
0.7303	Intermediate Similarity	NPD7154	Phase 3
0.7303	Intermediate Similarity	NPD5362	Discontinued
0.7234	Intermediate Similarity	NPD7983	Approved
0.7234	Intermediate Similarity	NPD6411	Approved
0.7191	Intermediate Similarity	NPD4269	Approved
0.7191	Intermediate Similarity	NPD4270	Approved
0.7159	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5779	Approved
0.7158	Intermediate Similarity	NPD5778	Approved
0.7037	Intermediate Similarity	NPD7331	Phase 2
0.6979	Remote Similarity	NPD6399	Phase 3
0.6966	Remote Similarity	NPD4819	Approved
0.6966	Remote Similarity	NPD4822	Approved
0.6966	Remote Similarity	NPD4821	Approved
0.6966	Remote Similarity	NPD4820	Approved
0.6966	Remote Similarity	NPD4252	Approved
0.6957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4271	Approved
0.6932	Remote Similarity	NPD4268	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6422	Discontinued
0.6869	Remote Similarity	NPD7902	Approved
0.6774	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7838	Discovery
0.6768	Remote Similarity	NPD7839	Suspended
0.6762	Remote Similarity	NPD6899	Approved
0.6762	Remote Similarity	NPD6881	Approved
0.6739	Remote Similarity	NPD5332	Approved
0.6739	Remote Similarity	NPD5331	Approved
0.6735	Remote Similarity	NPD7748	Approved
0.6731	Remote Similarity	NPD6402	Approved
0.6731	Remote Similarity	NPD7128	Approved
0.6731	Remote Similarity	NPD6675	Approved
0.6731	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD6650	Approved
0.6707	Remote Similarity	NPD7341	Phase 2
0.6703	Remote Similarity	NPD4790	Discontinued
0.6701	Remote Similarity	NPD7515	Phase 2
0.6698	Remote Similarity	NPD6372	Approved
0.6698	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7641	Discontinued
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6634	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4250	Approved
0.6632	Remote Similarity	NPD4251	Approved
0.663	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD7320	Approved
0.66	Remote Similarity	NPD4697	Phase 3
0.6585	Remote Similarity	NPD3197	Phase 1
0.6574	Remote Similarity	NPD8130	Phase 1
0.6574	Remote Similarity	NPD6847	Approved
0.6574	Remote Similarity	NPD6869	Approved
0.6574	Remote Similarity	NPD6617	Approved
0.6566	Remote Similarity	NPD7900	Approved
0.6566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5282	Discontinued
0.6542	Remote Similarity	NPD6012	Approved
0.6542	Remote Similarity	NPD6013	Approved
0.6542	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.6531	Remote Similarity	NPD6079	Approved
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD7146	Approved
0.6526	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD6409	Approved
0.6526	Remote Similarity	NPD4249	Approved
0.6514	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6514	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD5701	Approved
0.6495	Remote Similarity	NPD5328	Approved
0.6495	Remote Similarity	NPD1695	Approved
0.6471	Remote Similarity	NPD4225	Approved
0.6449	Remote Similarity	NPD6686	Approved
0.6444	Remote Similarity	NPD4756	Discovery
0.6422	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1694	Approved
0.6413	Remote Similarity	NPD4695	Discontinued
0.6392	Remote Similarity	NPD5737	Approved
0.6392	Remote Similarity	NPD6903	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD3618	Phase 1
0.6353	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5695	Phase 3
0.6327	Remote Similarity	NPD5370	Suspended
0.6316	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD5696	Approved
0.631	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3573	Approved
0.6282	Remote Similarity	NPD3194	Approved
0.6282	Remote Similarity	NPD4266	Approved
0.6282	Remote Similarity	NPD3195	Phase 2
0.6282	Remote Similarity	NPD3196	Approved
0.6277	Remote Similarity	NPD5209	Approved
0.6277	Remote Similarity	NPD3667	Approved
0.6275	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5221	Approved
0.6275	Remote Similarity	NPD5222	Approved
0.6265	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3704	Approved
0.6228	Remote Similarity	NPD6335	Approved
0.6222	Remote Similarity	NPD8039	Approved
0.6214	Remote Similarity	NPD5173	Approved
0.6214	Remote Similarity	NPD4755	Approved
0.6211	Remote Similarity	NPD6110	Phase 1
0.62	Remote Similarity	NPD8034	Phase 2
0.62	Remote Similarity	NPD5281	Approved
0.62	Remote Similarity	NPD8035	Phase 2
0.62	Remote Similarity	NPD7637	Suspended
0.62	Remote Similarity	NPD5284	Approved
0.62	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6274	Approved
0.6195	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6186	Remote Similarity	NPD5279	Phase 3
0.6174	Remote Similarity	NPD7101	Approved
0.6174	Remote Similarity	NPD7100	Approved
0.6162	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4632	Approved
0.6154	Remote Similarity	NPD3172	Approved
0.6146	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7115	Discovery
0.614	Remote Similarity	NPD6317	Approved
0.6132	Remote Similarity	NPD5224	Approved
0.6132	Remote Similarity	NPD5211	Phase 2
0.6132	Remote Similarity	NPD5226	Approved
0.6132	Remote Similarity	NPD4633	Approved
0.6132	Remote Similarity	NPD5225	Approved
0.6105	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7642	Approved
0.6098	Remote Similarity	NPD3198	Approved
0.6095	Remote Similarity	NPD4700	Approved
0.6087	Remote Similarity	NPD6313	Approved
0.6087	Remote Similarity	NPD6314	Approved
0.6076	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5175	Approved
0.6075	Remote Similarity	NPD5174	Approved
0.6075	Remote Similarity	NPD6647	Phase 2
0.6068	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6412	Phase 2
0.6047	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3732	Approved
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5141	Approved
0.6019	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD7507	Approved
0.5983	Remote Similarity	NPD6319	Approved
0.5982	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4202	Approved
0.5979	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD8328	Phase 3
0.5966	Remote Similarity	NPD7604	Phase 2
0.5962	Remote Similarity	NPD7614	Phase 1
0.5943	Remote Similarity	NPD6648	Approved
0.5932	Remote Similarity	NPD6909	Approved
0.5932	Remote Similarity	NPD5983	Phase 2
0.5932	Remote Similarity	NPD8516	Approved
0.5932	Remote Similarity	NPD8513	Phase 3

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