NPASS Compound

Structure

NPC474629 OpenBabel07101718282D 29 31 0 0 1 0 0 0 0 0999 V2000 -4.3395 -1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5800 1.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2499 3.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3226 2.1342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7140 2.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8480 -0.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7140 0.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9819 0.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6664 -0.9240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4076 -1.8900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8912 0.3007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9819 3.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8571 0.5595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8480 2.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2531 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6323 -0.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7140 1.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1159 2.5254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7346 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -2.1488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9819 1.0254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -0.4540 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1159 1.5254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8480 1.5254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1829 -3.1147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -0.5507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7820 -0.0000 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 16 1 0 0 0 0 2 17 2 0 0 0 0 3 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 17 25 1 0 0 0 0 18 24 1 6 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 6 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	439.902
LogP:	5.521
LogD:	4.475
LogS:	-4.698
# Rotatable Bonds:	7
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	4.656
Fsp3:	0.72
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:	-5.012
MDCK Permeability:	2.112448783009313e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	96.08592987060547%
Volume Distribution (VD):	0.858
Pgp-substrate:	3.144664764404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.447
CYP2C9-inhibitor:	0.4
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.832
CYP3A4-inhibitor:	0.357
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	7.84
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.158
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.634
Skin Sensitization:	0.684
Carcinogencity:	0.407
Eye Corrosion:	0.009
Eye Irritation:	0.063
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC474629

Natural Product ID:	NPC474629
*Common Name:**	Palauolol
IUPAC Name:	3-[(E,1R)-6-[(1S,2S,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-1-hydroxy-4-methylhex-3-enyl]-2-hydroxy-2H-furan-5-one
Synonyms:	Palauolol
Standard InCHIKey:	BSFHWMNYTJRBTJ-MYNQIBPASA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-16(9-10-20(26)19-15-22(27)29-23(19)28)11-13-24(4)18(3)12-14-25(5)17(2)7-6-8-21(24)25/h9,15,18,20-21,23,26,28H,2,6-8,10-14H2,1,3-5H3/b16-9+/t18-,20+,21+,23?,24-,25-/m0/s1
SMILES:	C/C(=CC[C@H](C1=CC(=O)OC1O)O)/CC[C@@]1(C)[C@@H](C)CC[C@@]2([C@@H]1CCCC2=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477722
PubChem CID:	44584726
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374971]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975486]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]

☑ 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	14

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT375	Cell Line	Malme-3M	Homo sapiens	IC50	=	0.46	ug.mL-1	PMID[558059]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	14.2	ug.mL-1	PMID[558059]
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[558060]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	2.2	ug.mL-1	PMID[558060]
NPT375	Cell Line	Malme-3M	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[558060]
NPT390	Cell Line	LOX IMVI	Homo sapiens	IC50	=	2.4	ug.mL-1	PMID[558060]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[558060]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1.3	ug.mL-1	PMID[558060]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	0.6	ug.mL-1	PMID[558060]
NPT386	Cell Line	KM12	Homo sapiens	IC50	=	1.8	ug.mL-1	PMID[558060]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[558060]
NPT383	Cell Line	SNB-19	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[558060]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7.0	ug.mL-1	PMID[558060]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.4	ug.mL-1	PMID[558060]

☑ 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 NPC474629 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	175
0.1-0.2	1142
0.2-0.3	4792
0.3-0.4	13087
0.4-0.5	10371
0.5-0.6	7043
0.6-0.7	5157
0.7-0.8	845
0.8-0.85	53
0.85-0.9	21
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9425	High Similarity	NPC469697
0.939	High Similarity	NPC42476
0.9294	High Similarity	NPC472810
0.9294	High Similarity	NPC472809
0.9213	High Similarity	NPC162346
0.9205	High Similarity	NPC298973
0.9205	High Similarity	NPC104925
0.9186	High Similarity	NPC470734
0.9091	High Similarity	NPC472812
0.9048	High Similarity	NPC126518
0.9036	High Similarity	NPC323251
0.8977	High Similarity	NPC472811
0.8941	High Similarity	NPC329630
0.8941	High Similarity	NPC163606
0.8901	High Similarity	NPC477718
0.8901	High Similarity	NPC477719
0.8864	High Similarity	NPC78973
0.8778	High Similarity	NPC470255
0.8721	High Similarity	NPC42586
0.8721	High Similarity	NPC473251
0.871	High Similarity	NPC477721
0.871	High Similarity	NPC477716
0.8706	High Similarity	NPC311070
0.8681	High Similarity	NPC472441
0.8617	High Similarity	NPC477717
0.8605	High Similarity	NPC470800
0.8605	High Similarity	NPC471302
0.8588	High Similarity	NPC471298
0.8571	High Similarity	NPC324078
0.8556	High Similarity	NPC477122
0.8556	High Similarity	NPC329842
0.8554	High Similarity	NPC474816
0.8554	High Similarity	NPC209135
0.8511	High Similarity	NPC324841
0.8495	Intermediate Similarity	NPC475709
0.8488	Intermediate Similarity	NPC471297
0.8444	Intermediate Similarity	NPC477782
0.8434	Intermediate Similarity	NPC262747
0.8434	Intermediate Similarity	NPC473756
0.8427	Intermediate Similarity	NPC472378
0.8409	Intermediate Similarity	NPC131813
0.8404	Intermediate Similarity	NPC474440
0.8372	Intermediate Similarity	NPC324170
0.8352	Intermediate Similarity	NPC477783
0.8333	Intermediate Similarity	NPC472815
0.8316	Intermediate Similarity	NPC477720
0.8295	Intermediate Similarity	NPC472442
0.8295	Intermediate Similarity	NPC217394
0.8283	Intermediate Similarity	NPC38948
0.828	Intermediate Similarity	NPC276110
0.8276	Intermediate Similarity	NPC472440
0.8261	Intermediate Similarity	NPC53555
0.8261	Intermediate Similarity	NPC242069
0.8256	Intermediate Similarity	NPC475944
0.8247	Intermediate Similarity	NPC120009
0.8242	Intermediate Similarity	NPC469403
0.8242	Intermediate Similarity	NPC232426
0.8242	Intermediate Similarity	NPC281942
0.8211	Intermediate Similarity	NPC473154
0.82	Intermediate Similarity	NPC206618
0.8182	Intermediate Similarity	NPC471301
0.8172	Intermediate Similarity	NPC474554
0.8172	Intermediate Similarity	NPC477722
0.8161	Intermediate Similarity	NPC471218
0.8152	Intermediate Similarity	NPC141831
0.8132	Intermediate Similarity	NPC174342
0.8132	Intermediate Similarity	NPC251528
0.8125	Intermediate Similarity	NPC38855
0.8111	Intermediate Similarity	NPC166857
0.8105	Intermediate Similarity	NPC98112
0.809	Intermediate Similarity	NPC471300
0.809	Intermediate Similarity	NPC474860
0.809	Intermediate Similarity	NPC471795
0.8068	Intermediate Similarity	NPC472377
0.8068	Intermediate Similarity	NPC474809
0.8065	Intermediate Similarity	NPC205034
0.8065	Intermediate Similarity	NPC162615
0.8065	Intermediate Similarity	NPC152778
0.8065	Intermediate Similarity	NPC469939
0.8061	Intermediate Similarity	NPC45897
0.8043	Intermediate Similarity	NPC182136
0.8041	Intermediate Similarity	NPC471075
0.8023	Intermediate Similarity	NPC242767
0.8021	Intermediate Similarity	NPC325229
0.8021	Intermediate Similarity	NPC275086
0.8	Intermediate Similarity	NPC17578
0.8	Intermediate Similarity	NPC16967
0.8	Intermediate Similarity	NPC165632
0.8	Intermediate Similarity	NPC240673
0.8	Intermediate Similarity	NPC475074
0.7979	Intermediate Similarity	NPC105490
0.7979	Intermediate Similarity	NPC474555
0.7978	Intermediate Similarity	NPC31086
0.7978	Intermediate Similarity	NPC474865
0.7957	Intermediate Similarity	NPC472814
0.7957	Intermediate Similarity	NPC177037
0.7957	Intermediate Similarity	NPC72845
0.7955	Intermediate Similarity	NPC471296
0.7952	Intermediate Similarity	NPC222244
0.7952	Intermediate Similarity	NPC16349
0.7938	Intermediate Similarity	NPC477972
0.7938	Intermediate Similarity	NPC161527
0.7938	Intermediate Similarity	NPC477968
0.7938	Intermediate Similarity	NPC219285
0.7938	Intermediate Similarity	NPC228251
0.7938	Intermediate Similarity	NPC477971
0.7938	Intermediate Similarity	NPC20113
0.7935	Intermediate Similarity	NPC474396
0.7935	Intermediate Similarity	NPC293044
0.7935	Intermediate Similarity	NPC79027
0.7935	Intermediate Similarity	NPC50488
0.7921	Intermediate Similarity	NPC470024
0.7917	Intermediate Similarity	NPC51499
0.7912	Intermediate Similarity	NPC312561
0.79	Intermediate Similarity	NPC218158
0.7889	Intermediate Similarity	NPC35933
0.7889	Intermediate Similarity	NPC474013
0.7889	Intermediate Similarity	NPC30984
0.7872	Intermediate Similarity	NPC472303
0.7872	Intermediate Similarity	NPC139692
0.7872	Intermediate Similarity	NPC472640
0.7872	Intermediate Similarity	NPC472641
0.7872	Intermediate Similarity	NPC7349
0.7872	Intermediate Similarity	NPC115021
0.7865	Intermediate Similarity	NPC23748
0.7865	Intermediate Similarity	NPC469
0.7865	Intermediate Similarity	NPC476927
0.7857	Intermediate Similarity	NPC63249
0.7849	Intermediate Similarity	NPC221111
0.7849	Intermediate Similarity	NPC280149
0.7849	Intermediate Similarity	NPC310479
0.7849	Intermediate Similarity	NPC472642
0.7849	Intermediate Similarity	NPC253186
0.7841	Intermediate Similarity	NPC170303
0.7841	Intermediate Similarity	NPC159148
0.7835	Intermediate Similarity	NPC278673
0.7826	Intermediate Similarity	NPC93411
0.7822	Intermediate Similarity	NPC471205
0.7822	Intermediate Similarity	NPC109376
0.7812	Intermediate Similarity	NPC473153
0.7812	Intermediate Similarity	NPC134072
0.7812	Intermediate Similarity	NPC234993
0.7812	Intermediate Similarity	NPC470801
0.7812	Intermediate Similarity	NPC242848
0.7802	Intermediate Similarity	NPC474062
0.7802	Intermediate Similarity	NPC329692
0.7802	Intermediate Similarity	NPC471219
0.7789	Intermediate Similarity	NPC191521
0.7789	Intermediate Similarity	NPC57117
0.7778	Intermediate Similarity	NPC238397
0.7778	Intermediate Similarity	NPC475038
0.7778	Intermediate Similarity	NPC471363
0.7778	Intermediate Similarity	NPC476081
0.7778	Intermediate Similarity	NPC134077
0.7778	Intermediate Similarity	NPC96055
0.7778	Intermediate Similarity	NPC109195
0.7766	Intermediate Similarity	NPC234335
0.7766	Intermediate Similarity	NPC289479
0.7755	Intermediate Similarity	NPC476767
0.7755	Intermediate Similarity	NPC472826
0.7755	Intermediate Similarity	NPC16601
0.7753	Intermediate Similarity	NPC256112
0.7753	Intermediate Similarity	NPC2524
0.7745	Intermediate Similarity	NPC300614
0.7745	Intermediate Similarity	NPC476765
0.7745	Intermediate Similarity	NPC392
0.7745	Intermediate Similarity	NPC325054
0.7745	Intermediate Similarity	NPC219900
0.7745	Intermediate Similarity	NPC177524
0.7745	Intermediate Similarity	NPC90946
0.7745	Intermediate Similarity	NPC224660
0.7742	Intermediate Similarity	NPC5509
0.7738	Intermediate Similarity	NPC476489
0.7738	Intermediate Similarity	NPC476490
0.7732	Intermediate Similarity	NPC73911
0.7727	Intermediate Similarity	NPC10636
0.7727	Intermediate Similarity	NPC281880
0.7723	Intermediate Similarity	NPC472818
0.7723	Intermediate Similarity	NPC172867
0.7717	Intermediate Similarity	NPC471796
0.7708	Intermediate Similarity	NPC275310
0.7708	Intermediate Similarity	NPC13924
0.7708	Intermediate Similarity	NPC286612
0.7708	Intermediate Similarity	NPC230347
0.77	Intermediate Similarity	NPC475889
0.77	Intermediate Similarity	NPC120321
0.77	Intermediate Similarity	NPC134270
0.77	Intermediate Similarity	NPC281378
0.77	Intermediate Similarity	NPC127933
0.77	Intermediate Similarity	NPC7613
0.77	Intermediate Similarity	NPC471938
0.77	Intermediate Similarity	NPC7644
0.7692	Intermediate Similarity	NPC106416
0.7692	Intermediate Similarity	NPC119001
0.7692	Intermediate Similarity	NPC65661
0.7692	Intermediate Similarity	NPC17791
0.7692	Intermediate Similarity	NPC86316
0.7692	Intermediate Similarity	NPC329738
0.7684	Intermediate Similarity	NPC156553
0.7684	Intermediate Similarity	NPC246860

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 NPC474629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1335
0.2-0.3	4065
0.3-0.4	2528
0.4-0.5	659
0.5-0.6	260
0.6-0.7	146
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD6400	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6686	Approved
0.7653	Intermediate Similarity	NPD4225	Approved
0.7576	Intermediate Similarity	NPD7639	Approved
0.7576	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7638	Approved
0.7396	Intermediate Similarity	NPD7637	Suspended
0.7363	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD7327	Approved
0.7232	Intermediate Similarity	NPD8033	Approved
0.7207	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD8294	Approved
0.7143	Intermediate Similarity	NPD8377	Approved
0.708	Intermediate Similarity	NPD8296	Approved
0.708	Intermediate Similarity	NPD8380	Approved
0.708	Intermediate Similarity	NPD8378	Approved
0.708	Intermediate Similarity	NPD8335	Approved
0.708	Intermediate Similarity	NPD8379	Approved
0.701	Intermediate Similarity	NPD6051	Approved
0.693	Remote Similarity	NPD7503	Approved
0.6923	Remote Similarity	NPD7632	Discontinued
0.6915	Remote Similarity	NPD6695	Phase 3
0.6875	Remote Similarity	NPD7115	Discovery
0.6863	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7507	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6813	Remote Similarity	NPD6925	Approved
0.6813	Remote Similarity	NPD5776	Phase 2
0.68	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD7514	Phase 3
0.6774	Remote Similarity	NPD7332	Phase 2
0.6768	Remote Similarity	NPD5785	Approved
0.6739	Remote Similarity	NPD7145	Approved
0.6739	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7748	Approved
0.6702	Remote Similarity	NPD6902	Approved
0.6701	Remote Similarity	NPD7146	Approved
0.6701	Remote Similarity	NPD7521	Approved
0.6701	Remote Similarity	NPD7334	Approved
0.6701	Remote Similarity	NPD6409	Approved
0.6701	Remote Similarity	NPD6684	Approved
0.6701	Remote Similarity	NPD5330	Approved
0.67	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6635	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7524	Approved
0.6633	Remote Similarity	NPD7750	Discontinued
0.66	Remote Similarity	NPD46	Approved
0.66	Remote Similarity	NPD6698	Approved
0.6596	Remote Similarity	NPD6931	Approved
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6930	Phase 2
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6593	Remote Similarity	NPD8264	Approved
0.6591	Remote Similarity	NPD6922	Approved
0.6591	Remote Similarity	NPD6923	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6574	Remote Similarity	NPD5739	Approved
0.6566	Remote Similarity	NPD6672	Approved
0.6566	Remote Similarity	NPD5737	Approved
0.6566	Remote Similarity	NPD6903	Approved
0.6566	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7154	Phase 3
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD6898	Phase 1
0.6522	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6882	Approved
0.6517	Remote Similarity	NPD7143	Approved
0.6517	Remote Similarity	NPD7144	Approved
0.6512	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5695	Phase 3
0.6495	Remote Similarity	NPD3666	Approved
0.6495	Remote Similarity	NPD3665	Phase 1
0.6495	Remote Similarity	NPD4786	Approved
0.6495	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD7645	Phase 2
0.6484	Remote Similarity	NPD6924	Approved
0.6484	Remote Similarity	NPD6926	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6458	Remote Similarity	NPD3667	Approved
0.6455	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6455	Remote Similarity	NPD6899	Approved
0.6452	Remote Similarity	NPD6932	Approved
0.6444	Remote Similarity	NPD7150	Approved
0.6444	Remote Similarity	NPD7152	Approved
0.6444	Remote Similarity	NPD7151	Approved
0.6436	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD7525	Registered
0.6415	Remote Similarity	NPD6648	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6395	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5362	Discontinued
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6373	Remote Similarity	NPD6411	Approved
0.6373	Remote Similarity	NPD5693	Phase 1
0.6373	Remote Similarity	NPD7087	Discontinued
0.6372	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6346	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6933	Approved
0.6339	Remote Similarity	NPD6883	Approved
0.6339	Remote Similarity	NPD7290	Approved
0.6339	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7102	Approved
0.6337	Remote Similarity	NPD5328	Approved
0.6337	Remote Similarity	NPD4753	Phase 2
0.6316	Remote Similarity	NPD6683	Phase 2
0.6316	Remote Similarity	NPD8133	Approved
0.63	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5209	Approved
0.6286	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6847	Approved
0.6283	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6283	Remote Similarity	NPD6617	Approved
0.6283	Remote Similarity	NPD8130	Phase 1
0.6263	Remote Similarity	NPD5363	Approved
0.6263	Remote Similarity	NPD6893	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD8297	Approved
0.6224	Remote Similarity	NPD5332	Approved
0.6224	Remote Similarity	NPD5331	Approved
0.6214	Remote Similarity	NPD6079	Approved
0.62	Remote Similarity	NPD4623	Approved
0.62	Remote Similarity	NPD4519	Discontinued
0.6195	Remote Similarity	NPD6371	Approved
0.6186	Remote Similarity	NPD4790	Discontinued
0.6176	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6080	Approved
0.6176	Remote Similarity	NPD6904	Approved
0.6176	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6673	Approved
0.6163	Remote Similarity	NPD4194	Approved
0.6163	Remote Similarity	NPD4192	Approved
0.6163	Remote Similarity	NPD4193	Approved
0.6163	Remote Similarity	NPD4191	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.6146	Remote Similarity	NPD4195	Approved
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6132	Remote Similarity	NPD7839	Suspended
0.6126	Remote Similarity	NPD6640	Phase 3
0.6122	Remote Similarity	NPD4270	Approved
0.6122	Remote Similarity	NPD4269	Approved
0.6117	Remote Similarity	NPD7136	Phase 2
0.6116	Remote Similarity	NPD8328	Phase 3
0.6106	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8293	Discontinued
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8513	Phase 3
0.6083	Remote Similarity	NPD8517	Approved
0.6082	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4252	Approved
0.6082	Remote Similarity	NPD4695	Discontinued
0.6082	Remote Similarity	NPD7509	Discontinued
0.6075	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD8039	Approved
0.6058	Remote Similarity	NPD8035	Phase 2
0.6058	Remote Similarity	NPD8034	Phase 2
0.6048	Remote Similarity	NPD7736	Approved
0.604	Remote Similarity	NPD4249	Approved
0.604	Remote Similarity	NPD5279	Phase 3
0.604	Remote Similarity	NPD5786	Approved
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4629	Approved
0.6038	Remote Similarity	NPD5210	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