NPASS Compound

Structure

NPC469677 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 0.1974 -1.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1062 2.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6263 -2.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9733 0.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2962 1.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3004 -1.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4344 -0.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4855 0.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6343 2.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 1.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1538 1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3980 -0.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6062 2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2992 -1.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9761 0.2172 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5082 0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1138 -0.5440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0712 1.2127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5037 0.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8282 -0.7905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8999 -1.1621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 23 1 1 0 0 0 20 5 1 6 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	355.825
LogP:	3.198
LogD:	3.747
LogS:	-4.254
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	5.004
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.614
MDCK Permeability:	2.490584483894054e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.88
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.485
Plasma Protein Binding (PPB):	98.83653259277344%
Volume Distribution (VD):	1.588
Pgp-substrate:	2.1867549419403076%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.29
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	6.89
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.783
Drug-inuced Liver Injury (DILI):	0.213
AMES Toxicity:	0.321
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.438
Carcinogencity:	0.094
Eye Corrosion:	0.079
Eye Irritation:	0.122
Respiratory Toxicity:	0.809

Download Data

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

Natural Product: NPC469677

Natural Product ID:	NPC469677
*Common Name:**	7R-Hydroperoxy-13-Keto-1R,11S*-Dolabell-3Z,8E,12(18)-Triene
IUPAC Name:	(3aR,5Z,9R,10E,12aR)-9-hydroperoxy-3a,6,10-trimethyl-1-propan-2-yl-1,3,4,7,8,9,12,12a-octahydrocyclopenta[11]annulen-2-one
Synonyms:
Standard InCHIKey:	CPQCREOKZWJGEH-HYXVUGABSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-13(2)19-16-8-7-15(4)18(23-22)9-6-14(3)10-11-20(16,5)12-17(19)21/h7,10,13,16,18-19,22H,6,8-9,11-12H2,1-5H3/b14-10-,15-7+/t16-,18-,19?,20-/m1/s1
SMILES:	OO[C@@H]1CC/C(=CC[C@]2([C@H](C/C=C/1C)C(C(C)C)C(=O)C2)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098221
PubChem CID:	46888281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	40900.0	nM	PMID[521286]

☑ 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 NPC469677 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	158
0.1-0.2	1434
0.2-0.3	10601
0.3-0.4	14510
0.4-0.5	7525
0.5-0.6	6151
0.6-0.7	2091
0.7-0.8	213
0.8-0.85	12
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9242	High Similarity	NPC469688
0.8955	High Similarity	NPC469679
0.8281	Intermediate Similarity	NPC267626
0.8281	Intermediate Similarity	NPC230823
0.8281	Intermediate Similarity	NPC49575
0.8281	Intermediate Similarity	NPC55004
0.8194	Intermediate Similarity	NPC107783
0.8194	Intermediate Similarity	NPC92909
0.8108	Intermediate Similarity	NPC469646
0.803	Intermediate Similarity	NPC259261
0.791	Intermediate Similarity	NPC25853
0.7879	Intermediate Similarity	NPC30215
0.7879	Intermediate Similarity	NPC266295
0.7879	Intermediate Similarity	NPC94991
0.7875	Intermediate Similarity	NPC474083
0.7875	Intermediate Similarity	NPC471224
0.7867	Intermediate Similarity	NPC279537
0.7867	Intermediate Similarity	NPC226242
0.7848	Intermediate Similarity	NPC470047
0.7848	Intermediate Similarity	NPC470046
0.7838	Intermediate Similarity	NPC167049
0.7838	Intermediate Similarity	NPC469691
0.7826	Intermediate Similarity	NPC473902
0.7794	Intermediate Similarity	NPC475795
0.7792	Intermediate Similarity	NPC469690
0.7763	Intermediate Similarity	NPC276769
0.7733	Intermediate Similarity	NPC216791
0.7733	Intermediate Similarity	NPC475771
0.7733	Intermediate Similarity	NPC251435
0.7733	Intermediate Similarity	NPC474011
0.7733	Intermediate Similarity	NPC469669
0.7733	Intermediate Similarity	NPC469678
0.7683	Intermediate Similarity	NPC317590
0.7662	Intermediate Similarity	NPC82635
0.7654	Intermediate Similarity	NPC470048
0.7625	Intermediate Similarity	NPC476082
0.7625	Intermediate Similarity	NPC278648
0.7619	Intermediate Similarity	NPC320026
0.76	Intermediate Similarity	NPC206875
0.7595	Intermediate Similarity	NPC4166
0.7564	Intermediate Similarity	NPC469620
0.7561	Intermediate Similarity	NPC469994
0.7561	Intermediate Similarity	NPC470051
0.7561	Intermediate Similarity	NPC470050
0.7534	Intermediate Similarity	NPC61702
0.7534	Intermediate Similarity	NPC162867
0.7532	Intermediate Similarity	NPC86917
0.7532	Intermediate Similarity	NPC91665
0.7531	Intermediate Similarity	NPC59453
0.7531	Intermediate Similarity	NPC230527
0.7531	Intermediate Similarity	NPC85774
0.7531	Intermediate Similarity	NPC221758
0.7531	Intermediate Similarity	NPC165064
0.7531	Intermediate Similarity	NPC82902
0.7531	Intermediate Similarity	NPC473246
0.7531	Intermediate Similarity	NPC214043
0.7531	Intermediate Similarity	NPC7927
0.7529	Intermediate Similarity	NPC473998
0.75	Intermediate Similarity	NPC20262
0.75	Intermediate Similarity	NPC309603
0.75	Intermediate Similarity	NPC473999
0.75	Intermediate Similarity	NPC256750
0.75	Intermediate Similarity	NPC123912
0.75	Intermediate Similarity	NPC2983
0.75	Intermediate Similarity	NPC311092
0.747	Intermediate Similarity	NPC287079
0.7465	Intermediate Similarity	NPC19569
0.7439	Intermediate Similarity	NPC474218
0.7439	Intermediate Similarity	NPC202868
0.7436	Intermediate Similarity	NPC474056
0.7436	Intermediate Similarity	NPC470052
0.7436	Intermediate Similarity	NPC475994
0.7436	Intermediate Similarity	NPC297996
0.7429	Intermediate Similarity	NPC165695
0.7412	Intermediate Similarity	NPC48010
0.7412	Intermediate Similarity	NPC69622
0.7407	Intermediate Similarity	NPC41539
0.7403	Intermediate Similarity	NPC215481
0.7397	Intermediate Similarity	NPC20610
0.7375	Intermediate Similarity	NPC47031
0.7375	Intermediate Similarity	NPC136150
0.7356	Intermediate Similarity	NPC8993
0.7349	Intermediate Similarity	NPC474778
0.7349	Intermediate Similarity	NPC474732
0.7349	Intermediate Similarity	NPC222613
0.7349	Intermediate Similarity	NPC474733
0.7349	Intermediate Similarity	NPC475022
0.7349	Intermediate Similarity	NPC51014
0.7349	Intermediate Similarity	NPC261253
0.7349	Intermediate Similarity	NPC118648
0.7349	Intermediate Similarity	NPC474045
0.7349	Intermediate Similarity	NPC31564
0.7349	Intermediate Similarity	NPC145879
0.7342	Intermediate Similarity	NPC229204
0.7342	Intermediate Similarity	NPC215843
0.7342	Intermediate Similarity	NPC181195
0.7342	Intermediate Similarity	NPC261125
0.7342	Intermediate Similarity	NPC7232
0.7342	Intermediate Similarity	NPC477371
0.7333	Intermediate Similarity	NPC471662
0.7326	Intermediate Similarity	NPC475806
0.7324	Intermediate Similarity	NPC309300
0.7324	Intermediate Similarity	NPC212210
0.7308	Intermediate Similarity	NPC470557
0.7308	Intermediate Similarity	NPC325946
0.7308	Intermediate Similarity	NPC74995
0.7297	Intermediate Similarity	NPC22301
0.7297	Intermediate Similarity	NPC182815
0.7294	Intermediate Similarity	NPC472971
0.7294	Intermediate Similarity	NPC170775
0.7294	Intermediate Similarity	NPC477215
0.7294	Intermediate Similarity	NPC476388
0.7294	Intermediate Similarity	NPC214387
0.7294	Intermediate Similarity	NPC472970
0.7286	Intermediate Similarity	NPC60565
0.7286	Intermediate Similarity	NPC97322
0.7286	Intermediate Similarity	NPC213152
0.7284	Intermediate Similarity	NPC151519
0.7284	Intermediate Similarity	NPC7414
0.7273	Intermediate Similarity	NPC77501
0.7262	Intermediate Similarity	NPC90652
0.7262	Intermediate Similarity	NPC475740
0.7262	Intermediate Similarity	NPC58063
0.726	Intermediate Similarity	NPC278895
0.725	Intermediate Similarity	NPC115418
0.725	Intermediate Similarity	NPC472478
0.725	Intermediate Similarity	NPC306095
0.725	Intermediate Similarity	NPC45495
0.7241	Intermediate Similarity	NPC37816
0.7241	Intermediate Similarity	NPC472930
0.7241	Intermediate Similarity	NPC69454
0.7241	Intermediate Similarity	NPC474736
0.7241	Intermediate Similarity	NPC472942
0.7241	Intermediate Similarity	NPC477520
0.7237	Intermediate Similarity	NPC470237
0.7237	Intermediate Similarity	NPC275098
0.7237	Intermediate Similarity	NPC303613
0.7237	Intermediate Similarity	NPC474228
0.7229	Intermediate Similarity	NPC474853
0.7229	Intermediate Similarity	NPC472940
0.7229	Intermediate Similarity	NPC470574
0.7229	Intermediate Similarity	NPC179006
0.7229	Intermediate Similarity	NPC472931
0.7229	Intermediate Similarity	NPC469948
0.7222	Intermediate Similarity	NPC477009
0.7222	Intermediate Similarity	NPC474329
0.7222	Intermediate Similarity	NPC474304
0.7222	Intermediate Similarity	NPC238352
0.7215	Intermediate Similarity	NPC192006
0.7215	Intermediate Similarity	NPC228911
0.7215	Intermediate Similarity	NPC469996
0.7209	Intermediate Similarity	NPC306168
0.7209	Intermediate Similarity	NPC49946
0.7209	Intermediate Similarity	NPC477147
0.7209	Intermediate Similarity	NPC477149
0.72	Intermediate Similarity	NPC159577
0.72	Intermediate Similarity	NPC307176
0.72	Intermediate Similarity	NPC477856
0.72	Intermediate Similarity	NPC214770
0.72	Intermediate Similarity	NPC35734
0.72	Intermediate Similarity	NPC282593
0.72	Intermediate Similarity	NPC40574
0.7195	Intermediate Similarity	NPC475622
0.7195	Intermediate Similarity	NPC108045
0.7191	Intermediate Similarity	NPC322063
0.7183	Intermediate Similarity	NPC32285
0.7179	Intermediate Similarity	NPC27205
0.7179	Intermediate Similarity	NPC271070
0.7176	Intermediate Similarity	NPC471722
0.7176	Intermediate Similarity	NPC193360
0.7176	Intermediate Similarity	NPC328313
0.7176	Intermediate Similarity	NPC470417
0.7162	Intermediate Similarity	NPC224532
0.7162	Intermediate Similarity	NPC167527
0.716	Intermediate Similarity	NPC147066
0.716	Intermediate Similarity	NPC38350
0.716	Intermediate Similarity	NPC477372
0.716	Intermediate Similarity	NPC101012
0.716	Intermediate Similarity	NPC88735
0.716	Intermediate Similarity	NPC201912
0.7143	Intermediate Similarity	NPC72133
0.7143	Intermediate Similarity	NPC471081
0.7143	Intermediate Similarity	NPC309852
0.7143	Intermediate Similarity	NPC89077
0.7143	Intermediate Similarity	NPC94755
0.7143	Intermediate Similarity	NPC473168
0.7143	Intermediate Similarity	NPC155011
0.7126	Intermediate Similarity	NPC190442
0.7126	Intermediate Similarity	NPC63748
0.7126	Intermediate Similarity	NPC221282
0.7126	Intermediate Similarity	NPC233116
0.7125	Intermediate Similarity	NPC90965
0.7125	Intermediate Similarity	NPC301769
0.7125	Intermediate Similarity	NPC308545
0.7125	Intermediate Similarity	NPC170793
0.7125	Intermediate Similarity	NPC308038
0.7125	Intermediate Similarity	NPC471299
0.7125	Intermediate Similarity	NPC472490
0.7125	Intermediate Similarity	NPC32758
0.7125	Intermediate Similarity	NPC201225

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 NPC469677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	2111
0.2-0.3	4536
0.3-0.4	1617
0.4-0.5	373
0.5-0.6	243
0.6-0.7	113
0.7-0.8	6
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
0.8378	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4786	Approved
0.7407	Intermediate Similarity	NPD5362	Discontinued
0.7284	Intermediate Similarity	NPD4270	Approved
0.7284	Intermediate Similarity	NPD4269	Approved
0.7284	Intermediate Similarity	NPD3667	Approved
0.725	Intermediate Similarity	NPD4252	Approved
0.72	Intermediate Similarity	NPD4747	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD5733	Approved
0.7108	Intermediate Similarity	NPD3668	Phase 3
0.7108	Intermediate Similarity	NPD3666	Approved
0.7108	Intermediate Similarity	NPD3665	Phase 1
0.7108	Intermediate Similarity	NPD3133	Approved
0.7105	Intermediate Similarity	NPD5276	Approved
0.7093	Intermediate Similarity	NPD5328	Approved
0.7067	Intermediate Similarity	NPD4137	Phase 3
0.7037	Intermediate Similarity	NPD5368	Approved
0.7024	Intermediate Similarity	NPD5363	Approved
0.7011	Intermediate Similarity	NPD5785	Approved
0.6988	Remote Similarity	NPD5332	Approved
0.6988	Remote Similarity	NPD5331	Approved
0.6974	Remote Similarity	NPD4691	Approved
0.6951	Remote Similarity	NPD5369	Approved
0.6951	Remote Similarity	NPD4790	Discontinued
0.6941	Remote Similarity	NPD6409	Approved
0.6941	Remote Similarity	NPD6684	Approved
0.6941	Remote Similarity	NPD7521	Approved
0.6941	Remote Similarity	NPD5786	Approved
0.6941	Remote Similarity	NPD3618	Phase 1
0.6941	Remote Similarity	NPD7146	Approved
0.6941	Remote Similarity	NPD5330	Approved
0.6941	Remote Similarity	NPD7334	Approved
0.6933	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6079	Approved
0.6923	Remote Similarity	NPD4687	Approved
0.6867	Remote Similarity	NPD4223	Phase 3
0.6867	Remote Similarity	NPD4221	Approved
0.6867	Remote Similarity	NPD6435	Approved
0.6854	Remote Similarity	NPD6399	Phase 3
0.6842	Remote Similarity	NPD6923	Approved
0.6842	Remote Similarity	NPD6922	Approved
0.6829	Remote Similarity	NPD4822	Approved
0.6829	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD4821	Approved
0.6829	Remote Similarity	NPD4819	Approved
0.6824	Remote Similarity	NPD5329	Approved
0.679	Remote Similarity	NPD4268	Approved
0.679	Remote Similarity	NPD4271	Approved
0.6786	Remote Similarity	NPD7154	Phase 3
0.6782	Remote Similarity	NPD6903	Approved
0.6782	Remote Similarity	NPD6672	Approved
0.6782	Remote Similarity	NPD5737	Approved
0.6782	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7143	Approved
0.6753	Remote Similarity	NPD7144	Approved
0.6709	Remote Similarity	NPD6924	Approved
0.6709	Remote Similarity	NPD6926	Approved
0.6709	Remote Similarity	NPD4058	Approved
0.6706	Remote Similarity	NPD4197	Approved
0.6705	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6628	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7514	Phase 3
0.6625	Remote Similarity	NPD8039	Approved
0.6588	Remote Similarity	NPD4788	Approved
0.6585	Remote Similarity	NPD7145	Approved
0.6585	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD6098	Approved
0.6552	Remote Similarity	NPD4138	Approved
0.6552	Remote Similarity	NPD4693	Phase 3
0.6552	Remote Similarity	NPD5280	Approved
0.6552	Remote Similarity	NPD4689	Approved
0.6552	Remote Similarity	NPD5690	Phase 2
0.6552	Remote Similarity	NPD4690	Approved
0.6552	Remote Similarity	NPD5205	Approved
0.6552	Remote Similarity	NPD4694	Approved
0.6552	Remote Similarity	NPD4688	Approved
0.6548	Remote Similarity	NPD6902	Approved
0.6543	Remote Similarity	NPD6933	Approved
0.6506	Remote Similarity	NPD6929	Approved
0.6471	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5209	Approved
0.6463	Remote Similarity	NPD6932	Approved
0.6452	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5221	Approved
0.6452	Remote Similarity	NPD4697	Phase 3
0.6452	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD1694	Approved
0.6437	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6931	Approved
0.6429	Remote Similarity	NPD6930	Phase 2
0.6429	Remote Similarity	NPD7332	Phase 2
0.642	Remote Similarity	NPD6942	Approved
0.642	Remote Similarity	NPD7339	Approved
0.6404	Remote Similarity	NPD4518	Approved
0.6386	Remote Similarity	NPD3617	Approved
0.6383	Remote Similarity	NPD4755	Approved
0.6383	Remote Similarity	NPD6083	Phase 2
0.6383	Remote Similarity	NPD6084	Phase 2
0.6383	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD4623	Approved
0.6353	Remote Similarity	NPD4139	Approved
0.6353	Remote Similarity	NPD4692	Approved
0.6344	Remote Similarity	NPD4629	Approved
0.6344	Remote Similarity	NPD5210	Approved
0.6344	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.6316	Remote Similarity	NPD7341	Phase 2
0.631	Remote Similarity	NPD6683	Phase 2
0.6289	Remote Similarity	NPD5211	Phase 2
0.6264	Remote Similarity	NPD4096	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.6235	Remote Similarity	NPD7525	Registered
0.6235	Remote Similarity	NPD4695	Discontinued
0.6222	Remote Similarity	NPD5208	Approved
0.622	Remote Similarity	NPD8264	Approved
0.6207	Remote Similarity	NPD6695	Phase 3
0.6196	Remote Similarity	NPD5281	Approved
0.6196	Remote Similarity	NPD6050	Approved
0.6196	Remote Similarity	NPD5284	Approved
0.6196	Remote Similarity	NPD5693	Phase 1
0.6196	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD5223	Approved
0.618	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD287	Approved
0.6163	Remote Similarity	NPD6898	Phase 1
0.6162	Remote Similarity	NPD5141	Approved
0.6154	Remote Similarity	NPD6051	Approved
0.6146	Remote Similarity	NPD5696	Approved
0.6146	Remote Similarity	NPD7638	Approved
0.6145	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD368	Approved
0.6122	Remote Similarity	NPD5224	Approved
0.6122	Remote Similarity	NPD4633	Approved
0.6122	Remote Similarity	NPD5226	Approved
0.6122	Remote Similarity	NPD5225	Approved
0.6118	Remote Similarity	NPD4195	Approved
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.6104	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6675	Approved
0.61	Remote Similarity	NPD7333	Discontinued
0.61	Remote Similarity	NPD5739	Approved
0.61	Remote Similarity	NPD7128	Approved
0.61	Remote Similarity	NPD6402	Approved
0.6092	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5207	Approved
0.6087	Remote Similarity	NPD5692	Phase 3
0.6082	Remote Similarity	NPD7640	Approved
0.6082	Remote Similarity	NPD7639	Approved
0.6081	Remote Similarity	NPD3198	Approved
0.6067	Remote Similarity	NPD6893	Approved
0.6064	Remote Similarity	NPD5282	Discontinued
0.6064	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6061	Remote Similarity	NPD4754	Approved
0.6049	Remote Similarity	NPD4243	Approved
0.6049	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7509	Discontinued
0.6023	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD8034	Phase 2
0.6022	Remote Similarity	NPD8035	Phase 2
0.6022	Remote Similarity	NPD5694	Approved
0.6022	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6899	Approved
0.5978	Remote Similarity	NPD5370	Suspended
0.5978	Remote Similarity	NPD1695	Approved
0.5977	Remote Similarity	NPD857	Phase 3
0.5974	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD3197	Phase 1
0.597	Remote Similarity	NPD344	Approved
0.597	Remote Similarity	NPD343	Approved
0.597	Remote Similarity	NPD345	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