NPASS Compound

Structure

CID49575 OpenBabel06191715382D 21 22 0 0 1 0 0 0 0 0999 V2000 -0.8737 -2.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4627 -2.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5551 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0350 1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4143 -0.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0426 -1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2251 0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -2.3843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3632 -1.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 1.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6182 0.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 -0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4692 -2.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 -2.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5350 0.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0712 -1.2127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9174 0.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1346 1.3741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 17 14 1 1 0 0 0 17 18 1 0 0 0 0 18 20 1 1 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	4.868
LogD:	4.384
LogS:	-5.236
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	4.513
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.668
MDCK Permeability:	2.110362402163446e-05
Pgp-inhibitor:	0.913
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.836
Plasma Protein Binding (PPB):	92.4743881225586%
Volume Distribution (VD):	1.934
Pgp-substrate:	3.6616499423980713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.303
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	8.377
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.672
Drug-inuced Liver Injury (DILI):	0.244
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.299
Skin Sensitization:	0.936
Carcinogencity:	0.603
Eye Corrosion:	0.796
Eye Irritation:	0.886
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC49575

Natural Product ID:	NPC49575
*Common Name:**	(1R,3Z,7E,11S,12S)-14-Oxo-3,7,18-Dolabellatriene
IUPAC Name:	(1S,3aR,5Z,9E,12aS)-3a,6,10-trimethyl-1-prop-1-en-2-yl-1,2,4,7,8,11,12,12a-octahydrocyclopenta[11]annulen-3-one
Synonyms:
Standard InCHIKey:	RNHJVFUOEQKJEA-SQJFUGCSSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-14(2)17-13-19(21)20(5)12-11-16(4)8-6-7-15(3)9-10-18(17)20/h7,11,17-18H,1,6,8-10,12-13H2,2-5H3/b15-7+,16-11-/t17-,18+,20-/m1/s1
SMILES:	C/C/1=C/C[C@@]2(C)C(=O)C[C@@H]([C@@H]2CC/C(=C/CC1)/C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689072
PubChem CID:	51039831
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
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	at a depth of 0.1-1 m, Elafonissos Island (3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	Elafonissos Island (GPS coordinates 3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29313	Halomonas meridiana	Species	Halomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29308	Mycobacterium marinum	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[548152]

☑ 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 NPC49575 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	3086
0.2-0.3	17799
0.3-0.4	10253
0.4-0.5	7231
0.5-0.6	3280
0.6-0.7	703
0.7-0.8	118
0.8-0.85	10
0.85-0.9	9
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55004
1.0	High Similarity	NPC267626
0.963	High Similarity	NPC230823
0.9464	High Similarity	NPC25853
0.9455	High Similarity	NPC94991
0.9455	High Similarity	NPC30215
0.9455	High Similarity	NPC266295
0.9286	High Similarity	NPC259261
0.8983	High Similarity	NPC473902
0.8966	High Similarity	NPC475795
0.8814	High Similarity	NPC165695
0.8644	High Similarity	NPC213152
0.8413	Intermediate Similarity	NPC20610
0.8361	Intermediate Similarity	NPC212210
0.8333	Intermediate Similarity	NPC97322
0.8305	Intermediate Similarity	NPC143834
0.8281	Intermediate Similarity	NPC182815
0.8281	Intermediate Similarity	NPC469677
0.8197	Intermediate Similarity	NPC32285
0.8182	Intermediate Similarity	NPC27438
0.8154	Intermediate Similarity	NPC477856
0.8154	Intermediate Similarity	NPC214770
0.8154	Intermediate Similarity	NPC282593
0.8154	Intermediate Similarity	NPC35734
0.8154	Intermediate Similarity	NPC159577
0.8154	Intermediate Similarity	NPC307176
0.8103	Intermediate Similarity	NPC20603
0.8095	Intermediate Similarity	NPC323005
0.807	Intermediate Similarity	NPC63396
0.807	Intermediate Similarity	NPC202850
0.8033	Intermediate Similarity	NPC60565
0.803	Intermediate Similarity	NPC115023
0.803	Intermediate Similarity	NPC470078
0.8	Intermediate Similarity	NPC285594
0.8	Intermediate Similarity	NPC96551
0.8	Intermediate Similarity	NPC139397
0.8	Intermediate Similarity	NPC162867
0.8	Intermediate Similarity	NPC61702
0.7969	Intermediate Similarity	NPC475523
0.7966	Intermediate Similarity	NPC115385
0.791	Intermediate Similarity	NPC251705
0.791	Intermediate Similarity	NPC107783
0.791	Intermediate Similarity	NPC470045
0.791	Intermediate Similarity	NPC303613
0.791	Intermediate Similarity	NPC474228
0.791	Intermediate Similarity	NPC92909
0.791	Intermediate Similarity	NPC470044
0.7903	Intermediate Similarity	NPC472306
0.7903	Intermediate Similarity	NPC197238
0.7903	Intermediate Similarity	NPC202118
0.7903	Intermediate Similarity	NPC167256
0.7895	Intermediate Similarity	NPC474141
0.7879	Intermediate Similarity	NPC251929
0.7879	Intermediate Similarity	NPC2634
0.7879	Intermediate Similarity	NPC260040
0.7879	Intermediate Similarity	NPC265782
0.7879	Intermediate Similarity	NPC40574
0.7869	Intermediate Similarity	NPC127582
0.7857	Intermediate Similarity	NPC236623
0.7846	Intermediate Similarity	NPC469688
0.7794	Intermediate Similarity	NPC309852
0.7778	Intermediate Similarity	NPC469662
0.7761	Intermediate Similarity	NPC234707
0.7761	Intermediate Similarity	NPC181204
0.7761	Intermediate Similarity	NPC54123
0.7761	Intermediate Similarity	NPC5701
0.7759	Intermediate Similarity	NPC95581
0.7681	Intermediate Similarity	NPC251435
0.7681	Intermediate Similarity	NPC293803
0.7679	Intermediate Similarity	NPC116906
0.7667	Intermediate Similarity	NPC193695
0.7656	Intermediate Similarity	NPC251118
0.7627	Intermediate Similarity	NPC275472
0.7627	Intermediate Similarity	NPC200258
0.7593	Intermediate Similarity	NPC49088
0.7586	Intermediate Similarity	NPC296311
0.7586	Intermediate Similarity	NPC268564
0.7581	Intermediate Similarity	NPC270042
0.7576	Intermediate Similarity	NPC469679
0.7571	Intermediate Similarity	NPC69408
0.7571	Intermediate Similarity	NPC226242
0.7541	Intermediate Similarity	NPC27610
0.7541	Intermediate Similarity	NPC56905
0.7538	Intermediate Similarity	NPC43300
0.7538	Intermediate Similarity	NPC39462
0.7538	Intermediate Similarity	NPC168824
0.7538	Intermediate Similarity	NPC96812
0.7538	Intermediate Similarity	NPC189917
0.7538	Intermediate Similarity	NPC107704
0.7536	Intermediate Similarity	NPC469691
0.7536	Intermediate Similarity	NPC167049
0.7536	Intermediate Similarity	NPC474797
0.7536	Intermediate Similarity	NPC474796
0.7536	Intermediate Similarity	NPC255021
0.7536	Intermediate Similarity	NPC329866
0.75	Intermediate Similarity	NPC6697
0.75	Intermediate Similarity	NPC305501
0.75	Intermediate Similarity	NPC285371
0.75	Intermediate Similarity	NPC475124
0.7465	Intermediate Similarity	NPC91665
0.7463	Intermediate Similarity	NPC256846
0.7455	Intermediate Similarity	NPC323445
0.7429	Intermediate Similarity	NPC77501
0.7429	Intermediate Similarity	NPC475771
0.7429	Intermediate Similarity	NPC255650
0.7429	Intermediate Similarity	NPC469678
0.7429	Intermediate Similarity	NPC469669
0.7419	Intermediate Similarity	NPC276764
0.7419	Intermediate Similarity	NPC472304
0.7377	Intermediate Similarity	NPC192427
0.7368	Intermediate Similarity	NPC32351
0.7361	Intermediate Similarity	NPC82635
0.7361	Intermediate Similarity	NPC470052
0.7361	Intermediate Similarity	NPC228911
0.7353	Intermediate Similarity	NPC151045
0.7353	Intermediate Similarity	NPC246722
0.7344	Intermediate Similarity	NPC288253
0.7324	Intermediate Similarity	NPC469793
0.7324	Intermediate Similarity	NPC469796
0.7324	Intermediate Similarity	NPC469646
0.7321	Intermediate Similarity	NPC91962
0.7313	Intermediate Similarity	NPC82477
0.7313	Intermediate Similarity	NPC39157
0.7313	Intermediate Similarity	NPC296697
0.7313	Intermediate Similarity	NPC155198
0.7313	Intermediate Similarity	NPC87141
0.7313	Intermediate Similarity	NPC142754
0.7313	Intermediate Similarity	NPC310992
0.7313	Intermediate Similarity	NPC188292
0.7313	Intermediate Similarity	NPC260474
0.7288	Intermediate Similarity	NPC45283
0.7286	Intermediate Similarity	NPC206875
0.7273	Intermediate Similarity	NPC176171
0.7273	Intermediate Similarity	NPC92327
0.726	Intermediate Similarity	NPC477371
0.726	Intermediate Similarity	NPC90965
0.726	Intermediate Similarity	NPC170793
0.726	Intermediate Similarity	NPC215843
0.7258	Intermediate Similarity	NPC170799
0.7258	Intermediate Similarity	NPC308108
0.7258	Intermediate Similarity	NPC311852
0.7246	Intermediate Similarity	NPC223187
0.7246	Intermediate Similarity	NPC304983
0.7241	Intermediate Similarity	NPC64866
0.7222	Intermediate Similarity	NPC470557
0.7222	Intermediate Similarity	NPC276769
0.7213	Intermediate Similarity	NPC473733
0.7206	Intermediate Similarity	NPC477857
0.7206	Intermediate Similarity	NPC286814
0.7193	Intermediate Similarity	NPC145311
0.7183	Intermediate Similarity	NPC473171
0.7164	Intermediate Similarity	NPC176107
0.7164	Intermediate Similarity	NPC220210
0.7164	Intermediate Similarity	NPC20181
0.7162	Intermediate Similarity	NPC474509
0.7143	Intermediate Similarity	NPC5698
0.7143	Intermediate Similarity	NPC300940
0.7143	Intermediate Similarity	NPC173996
0.7143	Intermediate Similarity	NPC83187
0.7143	Intermediate Similarity	NPC321017
0.7143	Intermediate Similarity	NPC8610
0.7143	Intermediate Similarity	NPC131981
0.7143	Intermediate Similarity	NPC285814
0.7143	Intermediate Similarity	NPC262558
0.7143	Intermediate Similarity	NPC98246
0.7143	Intermediate Similarity	NPC40249
0.7123	Intermediate Similarity	NPC474056
0.7123	Intermediate Similarity	NPC469996
0.7121	Intermediate Similarity	NPC183422
0.7121	Intermediate Similarity	NPC470329
0.7121	Intermediate Similarity	NPC268039
0.7119	Intermediate Similarity	NPC471751
0.7083	Intermediate Similarity	NPC215481
0.7067	Intermediate Similarity	NPC4166
0.7067	Intermediate Similarity	NPC147066
0.7067	Intermediate Similarity	NPC201912
0.7067	Intermediate Similarity	NPC38350
0.7067	Intermediate Similarity	NPC477372
0.7031	Intermediate Similarity	NPC252809
0.7031	Intermediate Similarity	NPC323153
0.7027	Intermediate Similarity	NPC469690
0.7018	Intermediate Similarity	NPC294440
0.7015	Intermediate Similarity	NPC154728
0.7015	Intermediate Similarity	NPC126899
0.7015	Intermediate Similarity	NPC304665
0.7	Intermediate Similarity	NPC23117
0.7	Intermediate Similarity	NPC190035
0.7	Intermediate Similarity	NPC469737
0.7	Intermediate Similarity	NPC133253
0.6984	Remote Similarity	NPC60772
0.6974	Remote Similarity	NPC311092
0.6974	Remote Similarity	NPC240302
0.6974	Remote Similarity	NPC260956
0.6974	Remote Similarity	NPC142253
0.6974	Remote Similarity	NPC3511
0.6974	Remote Similarity	NPC256750
0.6974	Remote Similarity	NPC20262
0.6974	Remote Similarity	NPC133391
0.6974	Remote Similarity	NPC193347
0.6974	Remote Similarity	NPC472239

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 NPC49575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	3306
0.2-0.3	4143
0.3-0.4	985
0.4-0.5	271
0.5-0.6	185
0.6-0.7	59
0.7-0.8	9
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
0.8154	Intermediate Similarity	NPD4747	Approved
0.8125	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD5276	Approved
0.8	Intermediate Similarity	NPD4137	Phase 3
0.7879	Intermediate Similarity	NPD4691	Approved
0.7794	Intermediate Similarity	NPD4687	Approved
0.7794	Intermediate Similarity	NPD5733	Approved
0.7536	Intermediate Similarity	NPD4058	Approved
0.7258	Intermediate Similarity	NPD287	Approved
0.7143	Intermediate Similarity	NPD343	Approved
0.7143	Intermediate Similarity	NPD344	Approved
0.7143	Intermediate Similarity	NPD345	Approved
0.7123	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4223	Phase 3
0.6974	Remote Similarity	NPD4221	Approved
0.6795	Remote Similarity	NPD4786	Approved
0.6795	Remote Similarity	NPD4197	Approved
0.6753	Remote Similarity	NPD3667	Approved
0.6709	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4138	Approved
0.6625	Remote Similarity	NPD4688	Approved
0.6625	Remote Similarity	NPD6098	Approved
0.6625	Remote Similarity	NPD4689	Approved
0.6625	Remote Similarity	NPD5280	Approved
0.6625	Remote Similarity	NPD4693	Phase 3
0.6625	Remote Similarity	NPD4690	Approved
0.6625	Remote Similarity	NPD5279	Phase 3
0.6625	Remote Similarity	NPD5690	Phase 2
0.6625	Remote Similarity	NPD5205	Approved
0.6625	Remote Similarity	NPD4694	Approved
0.6582	Remote Similarity	NPD3133	Approved
0.6582	Remote Similarity	NPD3665	Phase 1
0.6582	Remote Similarity	NPD3666	Approved
0.6582	Remote Similarity	NPD3668	Phase 3
0.6522	Remote Similarity	NPD7331	Phase 2
0.6481	Remote Similarity	NPD5783	Phase 3
0.6463	Remote Similarity	NPD6672	Approved
0.6463	Remote Similarity	NPD5737	Approved
0.6463	Remote Similarity	NPD4518	Approved
0.6463	Remote Similarity	NPD5208	Approved
0.6447	Remote Similarity	NPD3617	Approved
0.642	Remote Similarity	NPD7146	Approved
0.642	Remote Similarity	NPD7521	Approved
0.642	Remote Similarity	NPD3618	Phase 1
0.642	Remote Similarity	NPD5330	Approved
0.642	Remote Similarity	NPD7334	Approved
0.642	Remote Similarity	NPD6684	Approved
0.642	Remote Similarity	NPD6409	Approved
0.641	Remote Similarity	NPD4692	Approved
0.641	Remote Similarity	NPD4139	Approved
0.6386	Remote Similarity	NPD4753	Phase 2
0.6386	Remote Similarity	NPD5328	Approved
0.6386	Remote Similarity	NPD6904	Approved
0.6386	Remote Similarity	NPD6673	Approved
0.6386	Remote Similarity	NPD6080	Approved
0.631	Remote Similarity	NPD5207	Approved
0.631	Remote Similarity	NPD5692	Phase 3
0.631	Remote Similarity	NPD4096	Approved
0.6282	Remote Similarity	NPD4695	Discontinued
0.6282	Remote Similarity	NPD5368	Approved
0.6265	Remote Similarity	NPD6903	Approved
0.6265	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD6922	Approved
0.625	Remote Similarity	NPD5362	Discontinued
0.6235	Remote Similarity	NPD6079	Approved
0.6235	Remote Similarity	NPD5693	Phase 1
0.6235	Remote Similarity	NPD6050	Approved
0.6235	Remote Similarity	NPD5694	Approved
0.6235	Remote Similarity	NPD5284	Approved
0.6235	Remote Similarity	NPD5281	Approved
0.622	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5369	Approved
0.6164	Remote Similarity	NPD7143	Approved
0.6164	Remote Similarity	NPD7144	Approved
0.6163	Remote Similarity	NPD4202	Approved
0.6163	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD4195	Approved
0.6143	Remote Similarity	NPD7341	Phase 2
0.6125	Remote Similarity	NPD4270	Approved
0.6125	Remote Similarity	NPD4269	Approved
0.6125	Remote Similarity	NPD6435	Approved
0.6092	Remote Similarity	NPD6001	Approved
0.6081	Remote Similarity	NPD7151	Approved
0.6081	Remote Similarity	NPD4243	Approved
0.6081	Remote Similarity	NPD7152	Approved
0.6081	Remote Similarity	NPD7150	Approved
0.6076	Remote Similarity	NPD4252	Approved
0.6049	Remote Similarity	NPD4788	Approved
0.6024	Remote Similarity	NPD4519	Discontinued
0.6024	Remote Similarity	NPD4623	Approved
0.6023	Remote Similarity	NPD4629	Approved
0.6023	Remote Similarity	NPD5210	Approved
0.6023	Remote Similarity	NPD5695	Phase 3
0.6023	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8028	Phase 2
0.6	Remote Similarity	NPD857	Phase 3
0.5977	Remote Similarity	NPD5133	Approved
0.5955	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5222	Approved
0.5955	Remote Similarity	NPD5221	Approved
0.5955	Remote Similarity	NPD4697	Phase 3
0.593	Remote Similarity	NPD5785	Approved
0.5926	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4785	Approved
0.5921	Remote Similarity	NPD6924	Approved
0.5921	Remote Similarity	NPD4784	Approved
0.5921	Remote Similarity	NPD6926	Approved
0.5904	Remote Similarity	NPD5363	Approved
0.5889	Remote Similarity	NPD6084	Phase 2
0.5889	Remote Similarity	NPD6083	Phase 2
0.5889	Remote Similarity	NPD5173	Approved
0.5889	Remote Similarity	NPD4755	Approved
0.5873	Remote Similarity	NPD29	Approved
0.5873	Remote Similarity	NPD28	Approved
0.5854	Remote Similarity	NPD5332	Approved
0.5854	Remote Similarity	NPD5331	Approved
0.5844	Remote Similarity	NPD8039	Approved
0.5844	Remote Similarity	NPD7339	Approved
0.5844	Remote Similarity	NPD4190	Phase 3
0.5844	Remote Similarity	NPD6942	Approved
0.5844	Remote Similarity	NPD5275	Approved
0.5843	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD5786	Approved
0.5824	Remote Similarity	NPD5696	Approved
0.5802	Remote Similarity	NPD4790	Discontinued
0.5769	Remote Similarity	NPD6933	Approved
0.5765	Remote Similarity	NPD3573	Approved
0.5761	Remote Similarity	NPD4700	Approved
0.5761	Remote Similarity	NPD5286	Approved
0.5761	Remote Similarity	NPD4696	Approved
0.5761	Remote Similarity	NPD5285	Approved
0.5758	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD5209	Approved
0.573	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4191	Approved
0.5714	Remote Similarity	NPD4193	Approved
0.5714	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD5959	Approved
0.5714	Remote Similarity	NPD4194	Approved
0.5714	Remote Similarity	NPD4192	Approved
0.5699	Remote Similarity	NPD5223	Approved
0.5696	Remote Similarity	NPD6925	Approved
0.5696	Remote Similarity	NPD6932	Approved
0.5696	Remote Similarity	NPD5776	Phase 2
0.5694	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD3172	Approved
0.5679	Remote Similarity	NPD4821	Approved
0.5679	Remote Similarity	NPD4820	Approved
0.5679	Remote Similarity	NPD4822	Approved
0.5679	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD4819	Approved
0.5672	Remote Similarity	NPD4219	Approved
0.5663	Remote Similarity	NPD7154	Phase 3
0.5638	Remote Similarity	NPD5091	Approved
0.5638	Remote Similarity	NPD5226	Approved
0.5638	Remote Similarity	NPD5225	Approved
0.5638	Remote Similarity	NPD5224	Approved
0.5638	Remote Similarity	NPD5211	Phase 2
0.5638	Remote Similarity	NPD4633	Approved
0.5634	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4271	Approved
0.5625	Remote Similarity	NPD7145	Approved
0.5625	Remote Similarity	NPD4268	Approved
0.5616	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD4266	Approved
0.5606	Remote Similarity	NPD3196	Approved
0.5606	Remote Similarity	NPD3194	Approved
0.5606	Remote Similarity	NPD3195	Phase 2

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