NPASS Compound

Structure

NPC255650 OpenBabel07101718322D 31 35 0 0 1 0 0 0 0 0999 V2000 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 -6.5446 4.7859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 1 0 0 0 19 21 1 0 0 0 0 20 30 2 0 0 0 0 21 26 1 6 0 0 0 22 25 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 26 27 1 6 0 0 0 27 6 1 1 0 0 0 28 29 1 1 0 0 0 29 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.33
Volume:	477.029
LogP:	5.584
LogD:	4.538
LogS:	-5.405
# Rotatable Bonds:	4
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.478
Fsp3:	0.862
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:	-5.12
MDCK Permeability:	1.7791817299439572e-05
Pgp-inhibitor:	0.577
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.751
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	96.21206665039062%
Volume Distribution (VD):	1.139
Pgp-substrate:	1.8676666021347046%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.746
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.254
CYP2C9-substrate:	0.424
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.49
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	6.047
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.609
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.952
Carcinogencity:	0.451
Eye Corrosion:	0.567
Eye Irritation:	0.558
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC255650

Natural Product ID:	NPC255650
*Common Name:**	Vaticinone
IUPAC Name:	n.a.
Synonyms:	Vaticinone
Standard InCHIKey:	SRSDDLZWQZWBBZ-FFGFJAQXSA-N
Standard InCHI:	InChI=1S/C29H44O2/c1-19(8-7-9-20(2)30)21-12-14-27(6)23-11-10-22-25(3,4)24(31)13-15-28(22)18-29(23,28)17-16-26(21,27)5/h7,9,19,21-23H,8,10-18H2,1-6H3/b9-7+/t19-,21-,22+,23+,26-,27+,28-,29+/m1/s1
SMILES:	C[C@H](C/C=C/C(=O)C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)C(=O)CC[C@]54C[C@@]35CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498062
PubChem CID:	637226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	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
IC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	21500.0	nM	PMID[509228]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	15300.0	nM	PMID[509228]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.4	n.a.	PMID[509228]

☑ 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 NPC255650 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	201
0.1-0.2	2216
0.2-0.3	13025
0.3-0.4	12258
0.4-0.5	7911
0.5-0.6	5161
0.6-0.7	1646
0.7-0.8	223
0.8-0.85	24
0.85-0.9	25
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC69408
0.9296	High Similarity	NPC255021
0.9286	High Similarity	NPC234707
0.9286	High Similarity	NPC305501
0.9167	High Similarity	NPC293803
0.9155	High Similarity	NPC303613
0.9155	High Similarity	NPC474228
0.9155	High Similarity	NPC251705
0.9143	High Similarity	NPC477856
0.9143	High Similarity	NPC40574
0.9143	High Similarity	NPC214770
0.9028	High Similarity	NPC309852
0.9014	High Similarity	NPC54123
0.9014	High Similarity	NPC115023
0.9	High Similarity	NPC477857
0.8889	High Similarity	NPC470045
0.8889	High Similarity	NPC470044
0.8873	High Similarity	NPC307176
0.8873	High Similarity	NPC2634
0.8873	High Similarity	NPC251929
0.8873	High Similarity	NPC35734
0.8873	High Similarity	NPC282593
0.8873	High Similarity	NPC159577
0.8873	High Similarity	NPC265782
0.8816	High Similarity	NPC474509
0.8767	High Similarity	NPC329866
0.8767	High Similarity	NPC474796
0.8767	High Similarity	NPC474797
0.875	High Similarity	NPC5701
0.8732	High Similarity	NPC139397
0.8732	High Similarity	NPC182815
0.8611	High Similarity	NPC260040
0.8608	High Similarity	NPC178025
0.8608	High Similarity	NPC181743
0.8608	High Similarity	NPC16287
0.8592	High Similarity	NPC20610
0.8571	High Similarity	NPC107704
0.8571	High Similarity	NPC189917
0.8571	High Similarity	NPC96812
0.8571	High Similarity	NPC168824
0.8571	High Similarity	NPC323005
0.8571	High Similarity	NPC39462
0.8519	High Similarity	NPC476293
0.85	High Similarity	NPC60350
0.8493	Intermediate Similarity	NPC470078
0.8493	Intermediate Similarity	NPC225467
0.8451	Intermediate Similarity	NPC176107
0.8421	Intermediate Similarity	NPC470557
0.8421	Intermediate Similarity	NPC91665
0.84	Intermediate Similarity	NPC473171
0.8333	Intermediate Similarity	NPC260474
0.8333	Intermediate Similarity	NPC188292
0.831	Intermediate Similarity	NPC92327
0.8289	Intermediate Similarity	NPC469796
0.8289	Intermediate Similarity	NPC469793
0.8243	Intermediate Similarity	NPC190035
0.8219	Intermediate Similarity	NPC256846
0.8205	Intermediate Similarity	NPC90965
0.8205	Intermediate Similarity	NPC170793
0.8125	Intermediate Similarity	NPC472239
0.8125	Intermediate Similarity	NPC100297
0.8082	Intermediate Similarity	NPC87141
0.8077	Intermediate Similarity	NPC470052
0.8077	Intermediate Similarity	NPC82635
0.8072	Intermediate Similarity	NPC93778
0.8056	Intermediate Similarity	NPC43300
0.8052	Intermediate Similarity	NPC474463
0.8049	Intermediate Similarity	NPC29447
0.8028	Intermediate Similarity	NPC285371
0.8028	Intermediate Similarity	NPC212210
0.8028	Intermediate Similarity	NPC469662
0.8026	Intermediate Similarity	NPC159497
0.8	Intermediate Similarity	NPC181204
0.8	Intermediate Similarity	NPC223187
0.7975	Intermediate Similarity	NPC215843
0.7973	Intermediate Similarity	NPC286814
0.7917	Intermediate Similarity	NPC251118
0.7907	Intermediate Similarity	NPC23217
0.7901	Intermediate Similarity	NPC469804
0.7901	Intermediate Similarity	NPC142253
0.7901	Intermediate Similarity	NPC469805
0.7901	Intermediate Similarity	NPC3511
0.7901	Intermediate Similarity	NPC472867
0.7901	Intermediate Similarity	NPC320514
0.7887	Intermediate Similarity	NPC197238
0.7887	Intermediate Similarity	NPC202118
0.7887	Intermediate Similarity	NPC165695
0.7857	Intermediate Similarity	NPC25853
0.7848	Intermediate Similarity	NPC228911
0.7848	Intermediate Similarity	NPC115515
0.7848	Intermediate Similarity	NPC469996
0.7838	Intermediate Similarity	NPC39157
0.7838	Intermediate Similarity	NPC142754
0.7838	Intermediate Similarity	NPC310992
0.7838	Intermediate Similarity	NPC82477
0.7838	Intermediate Similarity	NPC296697
0.7808	Intermediate Similarity	NPC176171
0.7805	Intermediate Similarity	NPC474976
0.7805	Intermediate Similarity	NPC279639
0.7805	Intermediate Similarity	NPC3856
0.7805	Intermediate Similarity	NPC474790
0.7792	Intermediate Similarity	NPC211641
0.7763	Intermediate Similarity	NPC304983
0.775	Intermediate Similarity	NPC190211
0.7746	Intermediate Similarity	NPC60565
0.7746	Intermediate Similarity	NPC213152
0.7714	Intermediate Similarity	NPC259261
0.7711	Intermediate Similarity	NPC214043
0.7711	Intermediate Similarity	NPC85774
0.7711	Intermediate Similarity	NPC87552
0.7703	Intermediate Similarity	NPC220210
0.7703	Intermediate Similarity	NPC20181
0.7703	Intermediate Similarity	NPC475523
0.7701	Intermediate Similarity	NPC272746
0.7683	Intermediate Similarity	NPC193347
0.7683	Intermediate Similarity	NPC469799
0.7683	Intermediate Similarity	NPC469806
0.7674	Intermediate Similarity	NPC285982
0.7674	Intermediate Similarity	NPC262043
0.7662	Intermediate Similarity	NPC474488
0.7654	Intermediate Similarity	NPC472478
0.7654	Intermediate Similarity	NPC469797
0.7654	Intermediate Similarity	NPC469798
0.7647	Intermediate Similarity	NPC75315
0.7647	Intermediate Similarity	NPC58063
0.7647	Intermediate Similarity	NPC236618
0.7647	Intermediate Similarity	NPC163016
0.764	Intermediate Similarity	NPC476174
0.7639	Intermediate Similarity	NPC472306
0.7639	Intermediate Similarity	NPC288253
0.7632	Intermediate Similarity	NPC246722
0.7632	Intermediate Similarity	NPC151045
0.7625	Intermediate Similarity	NPC105197
0.7619	Intermediate Similarity	NPC8571
0.7619	Intermediate Similarity	NPC137493
0.7619	Intermediate Similarity	NPC469948
0.7619	Intermediate Similarity	NPC22133
0.7614	Intermediate Similarity	NPC478129
0.7614	Intermediate Similarity	NPC12722
0.7606	Intermediate Similarity	NPC127582
0.76	Intermediate Similarity	NPC155198
0.7595	Intermediate Similarity	NPC1254
0.759	Intermediate Similarity	NPC41539
0.7586	Intermediate Similarity	NPC126993
0.7571	Intermediate Similarity	NPC60772
0.7571	Intermediate Similarity	NPC266295
0.7571	Intermediate Similarity	NPC30215
0.7571	Intermediate Similarity	NPC94991
0.7564	Intermediate Similarity	NPC219232
0.7564	Intermediate Similarity	NPC128346
0.7561	Intermediate Similarity	NPC147066
0.7561	Intermediate Similarity	NPC477372
0.7561	Intermediate Similarity	NPC473217
0.7558	Intermediate Similarity	NPC117122
0.7558	Intermediate Similarity	NPC259252
0.7556	Intermediate Similarity	NPC29152
0.7536	Intermediate Similarity	NPC151464
0.7536	Intermediate Similarity	NPC143597
0.7536	Intermediate Similarity	NPC474105
0.7534	Intermediate Similarity	NPC475124
0.7534	Intermediate Similarity	NPC473902
0.7531	Intermediate Similarity	NPC158846
0.7529	Intermediate Similarity	NPC475022
0.7529	Intermediate Similarity	NPC474778
0.7529	Intermediate Similarity	NPC118648
0.7529	Intermediate Similarity	NPC186975
0.7529	Intermediate Similarity	NPC222613
0.7529	Intermediate Similarity	NPC145879
0.7529	Intermediate Similarity	NPC474732
0.7529	Intermediate Similarity	NPC474733
0.7529	Intermediate Similarity	NPC31564
0.7528	Intermediate Similarity	NPC294266
0.75	Intermediate Similarity	NPC218301
0.75	Intermediate Similarity	NPC473246
0.75	Intermediate Similarity	NPC475795
0.75	Intermediate Similarity	NPC144258
0.75	Intermediate Similarity	NPC237712
0.7473	Intermediate Similarity	NPC156546
0.7471	Intermediate Similarity	NPC474844
0.7471	Intermediate Similarity	NPC66344
0.747	Intermediate Similarity	NPC327969
0.747	Intermediate Similarity	NPC321289
0.7468	Intermediate Similarity	NPC476346
0.7465	Intermediate Similarity	NPC276764
0.7465	Intermediate Similarity	NPC472304
0.7444	Intermediate Similarity	NPC33473
0.7442	Intermediate Similarity	NPC136948
0.7442	Intermediate Similarity	NPC475740
0.7439	Intermediate Similarity	NPC476809
0.7436	Intermediate Similarity	NPC52667
0.7432	Intermediate Similarity	NPC470329
0.7429	Intermediate Similarity	NPC230823
0.7429	Intermediate Similarity	NPC267626
0.7429	Intermediate Similarity	NPC49575
0.7429	Intermediate Similarity	NPC192427
0.7429	Intermediate Similarity	NPC55004
0.7429	Intermediate Similarity	NPC115385
0.7416	Intermediate Similarity	NPC474807
0.7416	Intermediate Similarity	NPC474736
0.7412	Intermediate Similarity	NPC474537

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 NPC255650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2197
0.2-0.3	4655
0.3-0.4	1482
0.4-0.5	300
0.5-0.6	143
0.6-0.7	142
0.7-0.8	38
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8873	High Similarity	NPD4691	Approved
0.8873	High Similarity	NPD4747	Approved
0.8767	High Similarity	NPD4058	Approved
0.8732	High Similarity	NPD4137	Phase 3
0.8514	High Similarity	NPD5733	Approved
0.8514	High Similarity	NPD4687	Approved
0.8243	Intermediate Similarity	NPD5276	Approved
0.8082	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4221	Approved
0.7683	Intermediate Similarity	NPD4223	Phase 3
0.7619	Intermediate Similarity	NPD5329	Approved
0.759	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD4197	Approved
0.7356	Intermediate Similarity	NPD5737	Approved
0.7356	Intermediate Similarity	NPD6672	Approved
0.7356	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8028	Phase 2
0.7326	Intermediate Similarity	NPD7146	Approved
0.7326	Intermediate Similarity	NPD7334	Approved
0.7326	Intermediate Similarity	NPD4688	Approved
0.7326	Intermediate Similarity	NPD4693	Phase 3
0.7326	Intermediate Similarity	NPD7521	Approved
0.7326	Intermediate Similarity	NPD5330	Approved
0.7326	Intermediate Similarity	NPD5205	Approved
0.7326	Intermediate Similarity	NPD6409	Approved
0.7326	Intermediate Similarity	NPD4690	Approved
0.7326	Intermediate Similarity	NPD4138	Approved
0.7326	Intermediate Similarity	NPD4689	Approved
0.7326	Intermediate Similarity	NPD6684	Approved
0.7317	Intermediate Similarity	NPD4195	Approved
0.7294	Intermediate Similarity	NPD3666	Approved
0.7294	Intermediate Similarity	NPD4786	Approved
0.7294	Intermediate Similarity	NPD3665	Phase 1
0.7294	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD6673	Approved
0.7273	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD6904	Approved
0.7253	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3617	Approved
0.7176	Intermediate Similarity	NPD4788	Approved
0.7159	Intermediate Similarity	NPD6903	Approved
0.7159	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7126	Intermediate Similarity	NPD6098	Approved
0.7126	Intermediate Similarity	NPD4694	Approved
0.7126	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5280	Approved
0.7126	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD4753	Phase 2
0.7065	Intermediate Similarity	NPD5210	Approved
0.7065	Intermediate Similarity	NPD4629	Approved
0.7059	Intermediate Similarity	NPD3667	Approved
0.7024	Intermediate Similarity	NPD4695	Discontinued
0.7	Intermediate Similarity	NPD5207	Approved
0.6989	Remote Similarity	NPD5221	Approved
0.6989	Remote Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4519	Discontinued
0.6932	Remote Similarity	NPD4623	Approved
0.6932	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD5281	Approved
0.6923	Remote Similarity	NPD5284	Approved
0.6923	Remote Similarity	NPD5694	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD6050	Approved
0.6915	Remote Similarity	NPD5173	Approved
0.6897	Remote Similarity	NPD3668	Phase 3
0.6854	Remote Similarity	NPD3573	Approved
0.6849	Remote Similarity	NPD287	Approved
0.6848	Remote Similarity	NPD4202	Approved
0.6848	Remote Similarity	NPD5133	Approved
0.6813	Remote Similarity	NPD5692	Phase 3
0.6771	Remote Similarity	NPD5286	Approved
0.6771	Remote Similarity	NPD5285	Approved
0.6771	Remote Similarity	NPD4696	Approved
0.6737	Remote Similarity	NPD6083	Phase 2
0.6737	Remote Similarity	NPD6084	Phase 2
0.6701	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD5091	Approved
0.6633	Remote Similarity	NPD5226	Approved
0.6633	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4633	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6632	Remote Similarity	NPD4697	Phase 3
0.663	Remote Similarity	NPD4096	Approved
0.6596	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4518	Approved
0.6566	Remote Similarity	NPD5175	Approved
0.6566	Remote Similarity	NPD5174	Approved
0.6562	Remote Similarity	NPD5959	Approved
0.6562	Remote Similarity	NPD4755	Approved
0.6559	Remote Similarity	NPD7515	Phase 2
0.6552	Remote Similarity	NPD4692	Approved
0.6552	Remote Similarity	NPD4139	Approved
0.6535	Remote Similarity	NPD6614	Approved
0.6526	Remote Similarity	NPD5695	Phase 3
0.6522	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4784	Approved
0.6506	Remote Similarity	NPD4785	Approved
0.65	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5360	Phase 3
0.65	Remote Similarity	NPD5141	Approved
0.6495	Remote Similarity	NPD5696	Approved
0.6477	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6463	Remote Similarity	NPD4243	Approved
0.6444	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4700	Approved
0.6421	Remote Similarity	NPD7748	Approved
0.6421	Remote Similarity	NPD7900	Approved
0.6421	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6052	Approved
0.6395	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5697	Approved
0.6354	Remote Similarity	NPD5654	Approved
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6341	Remote Similarity	NPD4789	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD5168	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6289	Remote Similarity	NPD7614	Phase 1
0.6289	Remote Similarity	NPD7732	Phase 3
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6275	Remote Similarity	NPD6402	Approved
0.6275	Remote Similarity	NPD5739	Approved
0.6275	Remote Similarity	NPD7128	Approved
0.6275	Remote Similarity	NPD6675	Approved
0.6275	Remote Similarity	NPD6008	Approved
0.6265	Remote Similarity	NPD6081	Approved
0.6265	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6404	Discontinued
0.625	Remote Similarity	NPD7525	Registered
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD4224	Phase 2
0.625	Remote Similarity	NPD6013	Approved
0.6238	Remote Similarity	NPD4754	Approved
0.6235	Remote Similarity	NPD6942	Approved
0.6235	Remote Similarity	NPD7339	Approved
0.6226	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.6224	Remote Similarity	NPD7902	Approved
0.6224	Remote Similarity	NPD3495	Discontinued
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD4634	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5250	Approved
0.619	Remote Similarity	NPD5248	Approved
0.6162	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6147	Remote Similarity	NPD7115	Discovery
0.6145	Remote Similarity	NPD4245	Approved
0.6145	Remote Similarity	NPD7143	Approved
0.6145	Remote Similarity	NPD4244	Approved
0.6145	Remote Similarity	NPD7144	Approved
0.6132	Remote Similarity	NPD5127	Approved
0.6132	Remote Similarity	NPD5215	Approved
0.6132	Remote Similarity	NPD5216	Approved
0.6132	Remote Similarity	NPD5217	Approved
0.6125	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4768	Approved
0.6117	Remote Similarity	NPD4767	Approved
0.61	Remote Similarity	NPD7640	Approved
0.61	Remote Similarity	NPD7639	Approved
0.6095	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD6372	Approved
0.6087	Remote Similarity	NPD1694	Approved
0.6071	Remote Similarity	NPD7150	Approved
0.6071	Remote Similarity	NPD7152	Approved
0.6071	Remote Similarity	NPD5777	Approved
0.6071	Remote Similarity	NPD7151	Approved
0.6071	Remote Similarity	NPD4758	Discontinued
0.6058	Remote Similarity	NPD6412	Phase 2
0.6058	Remote Similarity	NPD5701	Approved
0.6055	Remote Similarity	NPD6868	Approved
0.6049	Remote Similarity	NPD7331	Phase 2
0.6047	Remote Similarity	NPD4190	Phase 3
0.6047	Remote Similarity	NPD5275	Approved
0.6042	Remote Similarity	NPD8035	Phase 2
0.6042	Remote Similarity	NPD8034	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