NPASS Compound

Structure

NPC159497 OpenBabel07101718282D 32 36 0 0 1 0 0 0 0 0999 V2000 -4.7056 -0.9418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5008 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0143 -0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1321 2.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0251 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1028 -1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7539 -0.7395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 0.1858 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 1 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 -3.4035 -2.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 31 2 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 27 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.35
Volume:	494.325
LogP:	5.93
LogD:	5.34
LogS:	-5.776
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	4.877
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.258
MDCK Permeability:	1.8553952031652443e-05
Pgp-inhibitor:	0.141
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	92.67366027832031%
Volume Distribution (VD):	1.215
Pgp-substrate:	1.6895787715911865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.667
CYP2C19-inhibitor:	0.209
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.4

ADMET: Excretion

Clearance (CL):	3.757
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.898
Carcinogencity:	0.025
Eye Corrosion:	0.969
Eye Irritation:	0.926
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC159497

Natural Product ID:	NPC159497
*Common Name:**	3-Oxolup-20(29)-En-30-Al
IUPAC Name:	2-[(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-1-yl]prop-2-enal
Synonyms:
Standard InCHIKey:	UULYNHWOJRYOFT-BHMAJAPKSA-N
Standard InCHI:	InChI=1S/C30H46O2/c1-19(18-31)20-10-13-27(4)16-17-29(6)21(25(20)27)8-9-23-28(5)14-12-24(32)26(2,3)22(28)11-15-30(23,29)7/h18,20-23,25H,1,8-17H2,2-7H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
SMILES:	O=CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581943
PubChem CID:	11848142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32825	cassine xylocarpa	Species	Celastraceae	Eukaryota	dried stems	Ahuachapan, El Salvado	n.a.	PMID[25927586]

☑ 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	4

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	CC50	=	5700.0	nM	PMID[485653]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[485653]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	1400.0	nM	PMID[485653]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	4.2	n.a.	PMID[485653]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	0.0	%	PMID[485653]

☑ 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 NPC159497 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	182
0.1-0.2	2898
0.2-0.3	16300
0.3-0.4	9537
0.4-0.5	6602
0.5-0.6	5147
0.6-0.7	1776
0.7-0.8	227
0.8-0.85	24
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC43300
0.8933	High Similarity	NPC474509
0.8857	High Similarity	NPC477857
0.8831	High Similarity	NPC175410
0.8429	Intermediate Similarity	NPC189917
0.8429	Intermediate Similarity	NPC107704
0.8429	Intermediate Similarity	NPC39462
0.8429	Intermediate Similarity	NPC168824
0.8429	Intermediate Similarity	NPC96812
0.8312	Intermediate Similarity	NPC201459
0.8312	Intermediate Similarity	NPC170793
0.8312	Intermediate Similarity	NPC90965
0.8293	Intermediate Similarity	NPC472739
0.8272	Intermediate Similarity	NPC269396
0.8272	Intermediate Similarity	NPC98236
0.8267	Intermediate Similarity	NPC293803
0.8243	Intermediate Similarity	NPC303613
0.8243	Intermediate Similarity	NPC474228
0.8182	Intermediate Similarity	NPC115515
0.8182	Intermediate Similarity	NPC63020
0.8158	Intermediate Similarity	NPC469793
0.8158	Intermediate Similarity	NPC469796
0.8133	Intermediate Similarity	NPC211641
0.8101	Intermediate Similarity	NPC103754
0.8101	Intermediate Similarity	NPC474484
0.8077	Intermediate Similarity	NPC471475
0.8052	Intermediate Similarity	NPC106078
0.8026	Intermediate Similarity	NPC255650
0.8025	Intermediate Similarity	NPC264665
0.8025	Intermediate Similarity	NPC74595
0.8	Intermediate Similarity	NPC251705
0.7973	Intermediate Similarity	NPC251929
0.7973	Intermediate Similarity	NPC214770
0.7973	Intermediate Similarity	NPC265782
0.7973	Intermediate Similarity	NPC307176
0.7973	Intermediate Similarity	NPC282593
0.7973	Intermediate Similarity	NPC477856
0.7973	Intermediate Similarity	NPC40574
0.7973	Intermediate Similarity	NPC159577
0.7973	Intermediate Similarity	NPC35734
0.7973	Intermediate Similarity	NPC2634
0.7949	Intermediate Similarity	NPC228911
0.7945	Intermediate Similarity	NPC20610
0.7922	Intermediate Similarity	NPC69408
0.7901	Intermediate Similarity	NPC472740
0.7901	Intermediate Similarity	NPC475726
0.7901	Intermediate Similarity	NPC472743
0.7895	Intermediate Similarity	NPC309852
0.7895	Intermediate Similarity	NPC128346
0.7895	Intermediate Similarity	NPC255021
0.7895	Intermediate Similarity	NPC219232
0.7867	Intermediate Similarity	NPC190035
0.7867	Intermediate Similarity	NPC115023
0.7867	Intermediate Similarity	NPC305501
0.7867	Intermediate Similarity	NPC54123
0.7867	Intermediate Similarity	NPC234707
0.7848	Intermediate Similarity	NPC192744
0.7838	Intermediate Similarity	NPC182815
0.7838	Intermediate Similarity	NPC286814
0.7838	Intermediate Similarity	NPC139397
0.7805	Intermediate Similarity	NPC474482
0.7805	Intermediate Similarity	NPC475745
0.7805	Intermediate Similarity	NPC474233
0.7763	Intermediate Similarity	NPC52667
0.7763	Intermediate Similarity	NPC470044
0.7763	Intermediate Similarity	NPC470045
0.7738	Intermediate Similarity	NPC93778
0.7733	Intermediate Similarity	NPC260040
0.7722	Intermediate Similarity	NPC82635
0.7714	Intermediate Similarity	NPC270042
0.7711	Intermediate Similarity	NPC292553
0.7711	Intermediate Similarity	NPC76518
0.7711	Intermediate Similarity	NPC201655
0.7703	Intermediate Similarity	NPC296697
0.7703	Intermediate Similarity	NPC142754
0.7703	Intermediate Similarity	NPC39157
0.7703	Intermediate Similarity	NPC82477
0.7703	Intermediate Similarity	NPC155198
0.7662	Intermediate Similarity	NPC474797
0.7662	Intermediate Similarity	NPC474796
0.7662	Intermediate Similarity	NPC329866
0.7647	Intermediate Similarity	NPC143597
0.7647	Intermediate Similarity	NPC151464
0.7632	Intermediate Similarity	NPC470078
0.7632	Intermediate Similarity	NPC225467
0.7619	Intermediate Similarity	NPC472738
0.7595	Intermediate Similarity	NPC68828
0.7595	Intermediate Similarity	NPC212661
0.7595	Intermediate Similarity	NPC471035
0.7595	Intermediate Similarity	NPC91665
0.7595	Intermediate Similarity	NPC470557
0.759	Intermediate Similarity	NPC475509
0.7568	Intermediate Similarity	NPC220210
0.7568	Intermediate Similarity	NPC20181
0.7561	Intermediate Similarity	NPC477858
0.7561	Intermediate Similarity	NPC145143
0.7532	Intermediate Similarity	NPC279241
0.7532	Intermediate Similarity	NPC474488
0.7531	Intermediate Similarity	NPC472478
0.7529	Intermediate Similarity	NPC57469
0.7529	Intermediate Similarity	NPC4643
0.75	Intermediate Similarity	NPC264317
0.75	Intermediate Similarity	NPC470052
0.75	Intermediate Similarity	NPC469996
0.75	Intermediate Similarity	NPC184819
0.75	Intermediate Similarity	NPC294438
0.75	Intermediate Similarity	NPC98270
0.75	Intermediate Similarity	NPC475700
0.7471	Intermediate Similarity	NPC169933
0.747	Intermediate Similarity	NPC471036
0.747	Intermediate Similarity	NPC291320
0.747	Intermediate Similarity	NPC118800
0.7442	Intermediate Similarity	NPC474719
0.7439	Intermediate Similarity	NPC164210
0.7432	Intermediate Similarity	NPC323005
0.7412	Intermediate Similarity	NPC471042
0.7412	Intermediate Similarity	NPC2783
0.7412	Intermediate Similarity	NPC12774
0.7407	Intermediate Similarity	NPC215843
0.7407	Intermediate Similarity	NPC472490
0.7403	Intermediate Similarity	NPC304983
0.7403	Intermediate Similarity	NPC474562
0.7403	Intermediate Similarity	NPC223187
0.7386	Intermediate Similarity	NPC272746
0.7381	Intermediate Similarity	NPC146683
0.7381	Intermediate Similarity	NPC178025
0.7381	Intermediate Similarity	NPC214043
0.7381	Intermediate Similarity	NPC85774
0.7381	Intermediate Similarity	NPC16287
0.7381	Intermediate Similarity	NPC181743
0.7375	Intermediate Similarity	NPC66105
0.7375	Intermediate Similarity	NPC149249
0.7353	Intermediate Similarity	NPC288296
0.7353	Intermediate Similarity	NPC53245
0.7349	Intermediate Similarity	NPC472239
0.7349	Intermediate Similarity	NPC142683
0.7342	Intermediate Similarity	NPC473171
0.7333	Intermediate Similarity	NPC280877
0.7333	Intermediate Similarity	NPC176107
0.7333	Intermediate Similarity	NPC290350
0.7333	Intermediate Similarity	NPC4370
0.7326	Intermediate Similarity	NPC269360
0.7326	Intermediate Similarity	NPC33768
0.7326	Intermediate Similarity	NPC264005
0.7317	Intermediate Similarity	NPC164999
0.7294	Intermediate Similarity	NPC190704
0.7294	Intermediate Similarity	NPC60350
0.7294	Intermediate Similarity	NPC471034
0.7294	Intermediate Similarity	NPC469948
0.7294	Intermediate Similarity	NPC33881
0.7294	Intermediate Similarity	NPC474971
0.7294	Intermediate Similarity	NPC102292
0.7273	Intermediate Similarity	NPC126993
0.7273	Intermediate Similarity	NPC85173
0.7273	Intermediate Similarity	NPC191684
0.7262	Intermediate Similarity	NPC470047
0.7262	Intermediate Similarity	NPC307258
0.7262	Intermediate Similarity	NPC41539
0.7262	Intermediate Similarity	NPC245866
0.7262	Intermediate Similarity	NPC470046
0.725	Intermediate Similarity	NPC246445
0.725	Intermediate Similarity	NPC474463
0.7241	Intermediate Similarity	NPC16377
0.7241	Intermediate Similarity	NPC4309
0.7241	Intermediate Similarity	NPC471900
0.7237	Intermediate Similarity	NPC188292
0.7237	Intermediate Similarity	NPC260474
0.7229	Intermediate Similarity	NPC4166
0.7229	Intermediate Similarity	NPC3915
0.7209	Intermediate Similarity	NPC474732
0.7209	Intermediate Similarity	NPC145879
0.7209	Intermediate Similarity	NPC474733
0.7209	Intermediate Similarity	NPC31564
0.7209	Intermediate Similarity	NPC70661
0.7209	Intermediate Similarity	NPC474778
0.7206	Intermediate Similarity	NPC127944
0.72	Intermediate Similarity	NPC92327
0.7195	Intermediate Similarity	NPC476812
0.7191	Intermediate Similarity	NPC23217
0.7191	Intermediate Similarity	NPC218301
0.7179	Intermediate Similarity	NPC5701
0.7176	Intermediate Similarity	NPC82902
0.7176	Intermediate Similarity	NPC237712
0.7176	Intermediate Similarity	NPC473246
0.7176	Intermediate Similarity	NPC59453
0.7176	Intermediate Similarity	NPC221758
0.7162	Intermediate Similarity	NPC169275
0.7162	Intermediate Similarity	NPC52449
0.7162	Intermediate Similarity	NPC212210
0.7162	Intermediate Similarity	NPC469662
0.716	Intermediate Similarity	NPC476811
0.7159	Intermediate Similarity	NPC116146
0.7159	Intermediate Similarity	NPC24772
0.7159	Intermediate Similarity	NPC247312
0.7159	Intermediate Similarity	NPC220498
0.7159	Intermediate Similarity	NPC213832
0.7159	Intermediate Similarity	NPC184663
0.7159	Intermediate Similarity	NPC271974
0.7159	Intermediate Similarity	NPC471043
0.7159	Intermediate Similarity	NPC469546

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 NPC159497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	3009
0.2-0.3	4431
0.3-0.4	1010
0.4-0.5	213
0.5-0.6	194
0.6-0.7	108
0.7-0.8	11
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
0.7973	Intermediate Similarity	NPD4691	Approved
0.7973	Intermediate Similarity	NPD4747	Approved
0.7901	Intermediate Similarity	NPD4788	Approved
0.7838	Intermediate Similarity	NPD4137	Phase 3
0.7662	Intermediate Similarity	NPD5733	Approved
0.7662	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4687	Approved
0.7403	Intermediate Similarity	NPD5276	Approved
0.7241	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4786	Approved
0.7045	Intermediate Similarity	NPD6672	Approved
0.7045	Intermediate Similarity	NPD5737	Approved
0.7011	Intermediate Similarity	NPD7521	Approved
0.7011	Intermediate Similarity	NPD7334	Approved
0.7011	Intermediate Similarity	NPD6684	Approved
0.7011	Intermediate Similarity	NPD5330	Approved
0.7011	Intermediate Similarity	NPD6409	Approved
0.7011	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD8035	Phase 2
0.7	Intermediate Similarity	NPD8034	Phase 2
0.6977	Remote Similarity	NPD3665	Phase 1
0.6977	Remote Similarity	NPD3133	Approved
0.6977	Remote Similarity	NPD3666	Approved
0.6966	Remote Similarity	NPD5328	Approved
0.6941	Remote Similarity	NPD4223	Phase 3
0.6941	Remote Similarity	NPD3667	Approved
0.6941	Remote Similarity	NPD4221	Approved
0.6897	Remote Similarity	NPD5329	Approved
0.6854	Remote Similarity	NPD6903	Approved
0.6835	Remote Similarity	NPD4789	Approved
0.6824	Remote Similarity	NPD8028	Phase 2
0.6818	Remote Similarity	NPD3618	Phase 1
0.6782	Remote Similarity	NPD4197	Approved
0.6782	Remote Similarity	NPD3668	Phase 3
0.6778	Remote Similarity	NPD4753	Phase 2
0.675	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3617	Approved
0.663	Remote Similarity	NPD7515	Phase 2
0.6629	Remote Similarity	NPD4138	Approved
0.6629	Remote Similarity	NPD6098	Approved
0.6629	Remote Similarity	NPD4689	Approved
0.6629	Remote Similarity	NPD4693	Phase 3
0.6629	Remote Similarity	NPD4688	Approved
0.6629	Remote Similarity	NPD4690	Approved
0.6629	Remote Similarity	NPD5690	Phase 2
0.6629	Remote Similarity	NPD5279	Phase 3
0.6629	Remote Similarity	NPD5205	Approved
0.6625	Remote Similarity	NPD4244	Approved
0.6625	Remote Similarity	NPD4245	Approved
0.6623	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4629	Approved
0.6596	Remote Similarity	NPD5210	Approved
0.6593	Remote Similarity	NPD6673	Approved
0.6593	Remote Similarity	NPD6080	Approved
0.6593	Remote Similarity	NPD6904	Approved
0.6582	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5360	Phase 3
0.6559	Remote Similarity	NPD6399	Phase 3
0.6559	Remote Similarity	NPD4202	Approved
0.6543	Remote Similarity	NPD5777	Approved
0.6526	Remote Similarity	NPD5221	Approved
0.6526	Remote Similarity	NPD5222	Approved
0.6526	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3698	Phase 2
0.65	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7748	Approved
0.6489	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5208	Approved
0.6458	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD5173	Approved
0.6458	Remote Similarity	NPD6083	Phase 2
0.6444	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4694	Approved
0.6444	Remote Similarity	NPD5280	Approved
0.6421	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4195	Approved
0.6386	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6081	Approved
0.6329	Remote Similarity	NPD4224	Phase 2
0.6327	Remote Similarity	NPD4696	Approved
0.6327	Remote Similarity	NPD5285	Approved
0.6327	Remote Similarity	NPD5286	Approved
0.6322	Remote Similarity	NPD4695	Discontinued
0.6289	Remote Similarity	NPD4755	Approved
0.6289	Remote Similarity	NPD7902	Approved
0.6277	Remote Similarity	NPD5693	Phase 1
0.6277	Remote Similarity	NPD6050	Approved
0.6263	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD4139	Approved
0.625	Remote Similarity	NPD4692	Approved
0.6235	Remote Similarity	NPD6117	Approved
0.6224	Remote Similarity	NPD5696	Approved
0.62	Remote Similarity	NPD5225	Approved
0.62	Remote Similarity	NPD5226	Approved
0.62	Remote Similarity	NPD5224	Approved
0.62	Remote Similarity	NPD4633	Approved
0.62	Remote Similarity	NPD5211	Phase 2
0.6196	Remote Similarity	NPD3573	Approved
0.618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5207	Approved
0.617	Remote Similarity	NPD5692	Phase 3
0.6163	Remote Similarity	NPD6116	Phase 1
0.6162	Remote Similarity	NPD4700	Approved
0.6146	Remote Similarity	NPD6001	Approved
0.6145	Remote Similarity	NPD4758	Discontinued
0.6139	Remote Similarity	NPD5174	Approved
0.6139	Remote Similarity	NPD5175	Approved
0.6136	Remote Similarity	NPD7525	Registered
0.6118	Remote Similarity	NPD6942	Approved
0.6118	Remote Similarity	NPD3703	Phase 2
0.6118	Remote Similarity	NPD7339	Approved
0.6105	Remote Similarity	NPD5694	Approved
0.6105	Remote Similarity	NPD5281	Approved
0.6105	Remote Similarity	NPD5284	Approved
0.6092	Remote Similarity	NPD6115	Approved
0.6092	Remote Similarity	NPD4777	Suspended
0.6092	Remote Similarity	NPD4776	Phase 2
0.6092	Remote Similarity	NPD6118	Approved
0.6092	Remote Similarity	NPD6114	Approved
0.6092	Remote Similarity	NPD6697	Approved
0.6087	Remote Similarity	NPD4519	Discontinued
0.6087	Remote Similarity	NPD4623	Approved
0.6078	Remote Similarity	NPD5141	Approved
0.6064	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD287	Approved
0.602	Remote Similarity	NPD7732	Phase 3
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4096	Approved
0.598	Remote Similarity	NPD4754	Approved
0.5962	Remote Similarity	NPD5697	Approved
0.5962	Remote Similarity	NPD6412	Phase 2
0.5952	Remote Similarity	NPD4243	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.593	Remote Similarity	NPD3702	Approved
0.5909	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5364	Discontinued
0.5909	Remote Similarity	NPD3671	Phase 1
0.5905	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD5168	Approved
0.5905	Remote Similarity	NPD4730	Approved
0.5905	Remote Similarity	NPD5128	Approved
0.5905	Remote Similarity	NPD4729	Approved
0.5905	Remote Similarity	NPD7320	Approved
0.5904	Remote Similarity	NPD6923	Approved
0.5904	Remote Similarity	NPD6922	Approved
0.59	Remote Similarity	NPD7638	Approved
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD5091	Approved
0.5876	Remote Similarity	NPD5133	Approved
0.5865	Remote Similarity	NPD4767	Approved
0.5865	Remote Similarity	NPD4768	Approved
0.5865	Remote Similarity	NPD6008	Approved
0.5862	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7614	Phase 1
0.5857	Remote Similarity	NPD344	Approved
0.5857	Remote Similarity	NPD343	Approved
0.5857	Remote Similarity	NPD345	Approved
0.5849	Remote Similarity	NPD6372	Approved
0.5849	Remote Similarity	NPD6013	Approved
0.5849	Remote Similarity	NPD6014	Approved
0.5849	Remote Similarity	NPD6012	Approved
0.5849	Remote Similarity	NPD6373	Approved
0.5843	Remote Similarity	NPD7645	Phase 2
0.5842	Remote Similarity	NPD7639	Approved
0.5842	Remote Similarity	NPD7640	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD7143	Approved
0.5833	Remote Similarity	NPD7144	Approved
0.5825	Remote Similarity	NPD6052	Approved
0.5816	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4785	Approved
0.5814	Remote Similarity	NPD6926	Approved
0.5814	Remote Similarity	NPD6924	Approved
0.5814	Remote Similarity	NPD4784	Approved
0.581	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD6614	Approved
0.5794	Remote Similarity	NPD5135	Approved
0.5794	Remote Similarity	NPD5248	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