NPASS Compound

Structure

NPC474797 OpenBabel07101719252D 33 35 0 0 1 0 0 0 0 0999 V2000 -3.5254 -2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8199 -1.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.6340 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 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4598 -3.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4817 -3.0428 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 1.7321 3.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1290 -2.5075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 -2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 2 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 -8.1071 -2.7155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8418 -1.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 28 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 19 26 2 0 0 0 0 20 30 2 0 0 0 0 21 31 2 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 26 29 1 0 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.28
Volume:	498.54
LogP:	3.876
LogD:	3.491
LogS:	-5.059
# Rotatable Bonds:	5
TPSA:	68.28
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	4.616
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043
MDCK Permeability:	2.144057179975789e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	91.07382202148438%
Volume Distribution (VD):	1.2
Pgp-substrate:	5.802897930145264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.593
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.506
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.437
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.803
CYP3A4-substrate:	0.779

ADMET: Excretion

Clearance (CL):	5.708
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.538
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.609
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.865
Carcinogencity:	0.86
Eye Corrosion:	0.007
Eye Irritation:	0.264
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC474797

Natural Product ID:	NPC474797
*Common Name:**	Isogeoditin A
IUPAC Name:	(3Z,3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-3-[(3E,5E,8Z)-6-methyl-7,10-dioxoundeca-3,5,8-trien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione
Synonyms:
Standard InCHIKey:	LZZDDKOYYZTLIC-SLXXOZHFSA-N
Standard InCHI:	InChI=1S/C29H38O4/c1-18(21(31)12-11-20(3)30)9-8-10-19(2)26-22(32)17-24-28(6)16-14-25(33)27(4,5)23(28)13-15-29(24,26)7/h8-12,23-24H,13-17H2,1-7H3/b10-8+,12-11-,18-9+,26-19+/t23-,24-,28-,29-/m0/s1
SMILES:	CC(=O)/C=CC(=O)/C(=C/C=C/C(=C/1C(=O)C[C@@H]2[C@]1(C)CC[C@@H]1[C@]2(C)CCC(=O)C1(C)C)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483013
PubChem CID:	21574215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620246]
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18826276]

☑ 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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.13	ug.mL-1	PMID[569198]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.35	ug.mL-1	PMID[569198]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	0.47	ug.mL-1	PMID[569198]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3.7	ug.mL-1	PMID[569198]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.07	ug.mL-1	PMID[569198]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.2	ug.mL-1	PMID[569198]

☑ 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 NPC474797 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	171
0.1-0.2	1506
0.2-0.3	7873
0.3-0.4	16018
0.4-0.5	8777
0.5-0.6	5926
0.6-0.7	1967
0.7-0.8	391
0.8-0.85	27
0.85-0.9	28
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474796
1.0	High Similarity	NPC329866
0.9167	High Similarity	NPC469793
0.9167	High Similarity	NPC469796
0.9143	High Similarity	NPC54123
0.9028	High Similarity	NPC473171
0.9014	High Similarity	NPC474228
0.9014	High Similarity	NPC303613
0.9014	High Similarity	NPC251705
0.9	High Similarity	NPC265782
0.9	High Similarity	NPC251929
0.9	High Similarity	NPC2634
0.8947	High Similarity	NPC469804
0.8947	High Similarity	NPC469805
0.8904	High Similarity	NPC69408
0.8889	High Similarity	NPC309852
0.8873	High Similarity	NPC115023
0.8873	High Similarity	NPC234707
0.8873	High Similarity	NPC305501
0.8873	High Similarity	NPC470078
0.8857	High Similarity	NPC139397
0.8831	High Similarity	NPC279639
0.8831	High Similarity	NPC3856
0.8831	High Similarity	NPC474976
0.8831	High Similarity	NPC474790
0.8767	High Similarity	NPC293803
0.8767	High Similarity	NPC255650
0.875	High Similarity	NPC470044
0.875	High Similarity	NPC470045
0.8732	High Similarity	NPC35734
0.8732	High Similarity	NPC260040
0.8732	High Similarity	NPC159577
0.8732	High Similarity	NPC282593
0.8732	High Similarity	NPC307176
0.8701	High Similarity	NPC469806
0.8701	High Similarity	NPC469799
0.8684	High Similarity	NPC469798
0.8684	High Similarity	NPC469797
0.863	High Similarity	NPC255021
0.8611	High Similarity	NPC181204
0.8592	High Similarity	NPC182815
0.8592	High Similarity	NPC256846
0.8553	High Similarity	NPC170793
0.8472	Intermediate Similarity	NPC40574
0.8451	Intermediate Similarity	NPC260474
0.8451	Intermediate Similarity	NPC188292
0.8451	Intermediate Similarity	NPC20610
0.8451	Intermediate Similarity	NPC310992
0.8442	Intermediate Similarity	NPC474509
0.8429	Intermediate Similarity	NPC323005
0.8406	Intermediate Similarity	NPC212210
0.8395	Intermediate Similarity	NPC163016
0.8395	Intermediate Similarity	NPC75315
0.8356	Intermediate Similarity	NPC5701
0.831	Intermediate Similarity	NPC176107
0.8286	Intermediate Similarity	NPC251118
0.8219	Intermediate Similarity	NPC477856
0.8219	Intermediate Similarity	NPC214770
0.8194	Intermediate Similarity	NPC87141
0.8193	Intermediate Similarity	NPC474844
0.8171	Intermediate Similarity	NPC476293
0.8169	Intermediate Similarity	NPC92327
0.8143	Intermediate Similarity	NPC469662
0.8116	Intermediate Similarity	NPC60565
0.8108	Intermediate Similarity	NPC223187
0.8108	Intermediate Similarity	NPC225467
0.8108	Intermediate Similarity	NPC190035
0.8095	Intermediate Similarity	NPC475965
0.8095	Intermediate Similarity	NPC474842
0.8088	Intermediate Similarity	NPC259261
0.8082	Intermediate Similarity	NPC477857
0.8077	Intermediate Similarity	NPC90965
0.8056	Intermediate Similarity	NPC475523
0.8052	Intermediate Similarity	NPC91665
0.8025	Intermediate Similarity	NPC87552
0.8	Intermediate Similarity	NPC197238
0.8	Intermediate Similarity	NPC288253
0.8	Intermediate Similarity	NPC202118
0.8	Intermediate Similarity	NPC474018
0.8	Intermediate Similarity	NPC472239
0.8	Intermediate Similarity	NPC473986
0.8	Intermediate Similarity	NPC165695
0.7971	Intermediate Similarity	NPC127582
0.7971	Intermediate Similarity	NPC25853
0.7952	Intermediate Similarity	NPC141292
0.7949	Intermediate Similarity	NPC470052
0.7949	Intermediate Similarity	NPC82635
0.7949	Intermediate Similarity	NPC228911
0.7945	Intermediate Similarity	NPC155198
0.7941	Intermediate Similarity	NPC266295
0.7941	Intermediate Similarity	NPC94991
0.7941	Intermediate Similarity	NPC60772
0.7927	Intermediate Similarity	NPC60350
0.7927	Intermediate Similarity	NPC29447
0.7922	Intermediate Similarity	NPC474463
0.7917	Intermediate Similarity	NPC176171
0.7887	Intermediate Similarity	NPC475124
0.7887	Intermediate Similarity	NPC285371
0.7887	Intermediate Similarity	NPC4638
0.7857	Intermediate Similarity	NPC213152
0.7857	Intermediate Similarity	NPC292491
0.7857	Intermediate Similarity	NPC310752
0.7838	Intermediate Similarity	NPC286814
0.7826	Intermediate Similarity	NPC276764
0.7826	Intermediate Similarity	NPC472304
0.7821	Intermediate Similarity	NPC470557
0.7816	Intermediate Similarity	NPC299100
0.7805	Intermediate Similarity	NPC16287
0.7805	Intermediate Similarity	NPC178025
0.7805	Intermediate Similarity	NPC181743
0.7794	Intermediate Similarity	NPC230823
0.7794	Intermediate Similarity	NPC115385
0.7792	Intermediate Similarity	NPC476346
0.7792	Intermediate Similarity	NPC469803
0.7791	Intermediate Similarity	NPC204341
0.7778	Intermediate Similarity	NPC472867
0.7778	Intermediate Similarity	NPC320514
0.7778	Intermediate Similarity	NPC142253
0.7778	Intermediate Similarity	NPC268039
0.7778	Intermediate Similarity	NPC100297
0.7778	Intermediate Similarity	NPC94200
0.7778	Intermediate Similarity	NPC3511
0.7765	Intermediate Similarity	NPC262043
0.7746	Intermediate Similarity	NPC32285
0.7746	Intermediate Similarity	NPC472306
0.7738	Intermediate Similarity	NPC93778
0.7727	Intermediate Similarity	NPC180950
0.7722	Intermediate Similarity	NPC469996
0.7722	Intermediate Similarity	NPC115515
0.7722	Intermediate Similarity	NPC189485
0.7711	Intermediate Similarity	NPC8571
0.7703	Intermediate Similarity	NPC296697
0.7703	Intermediate Similarity	NPC142754
0.7703	Intermediate Similarity	NPC39157
0.7703	Intermediate Similarity	NPC82477
0.7692	Intermediate Similarity	NPC1254
0.7683	Intermediate Similarity	NPC118423
0.7681	Intermediate Similarity	NPC311852
0.7681	Intermediate Similarity	NPC30215
0.7681	Intermediate Similarity	NPC27610
0.7681	Intermediate Similarity	NPC56905
0.7671	Intermediate Similarity	NPC168824
0.7671	Intermediate Similarity	NPC39462
0.7671	Intermediate Similarity	NPC43300
0.7671	Intermediate Similarity	NPC107704
0.7671	Intermediate Similarity	NPC189917
0.7671	Intermediate Similarity	NPC96812
0.7662	Intermediate Similarity	NPC219232
0.7662	Intermediate Similarity	NPC211641
0.7662	Intermediate Similarity	NPC159497
0.7662	Intermediate Similarity	NPC128346
0.7662	Intermediate Similarity	NPC20025
0.7654	Intermediate Similarity	NPC470034
0.7654	Intermediate Similarity	NPC4166
0.7654	Intermediate Similarity	NPC278459
0.7654	Intermediate Similarity	NPC477372
0.7654	Intermediate Similarity	NPC475863
0.764	Intermediate Similarity	NPC122324
0.764	Intermediate Similarity	NPC151725
0.764	Intermediate Similarity	NPC301534
0.764	Intermediate Similarity	NPC106425
0.764	Intermediate Similarity	NPC250757
0.7639	Intermediate Similarity	NPC473902
0.7632	Intermediate Similarity	NPC133253
0.7632	Intermediate Similarity	NPC21944
0.7632	Intermediate Similarity	NPC474562
0.7625	Intermediate Similarity	NPC215843
0.7625	Intermediate Similarity	NPC27817
0.7625	Intermediate Similarity	NPC190211
0.7619	Intermediate Similarity	NPC168248
0.7614	Intermediate Similarity	NPC473280
0.7614	Intermediate Similarity	NPC471078
0.7614	Intermediate Similarity	NPC473435
0.7614	Intermediate Similarity	NPC473431
0.7614	Intermediate Similarity	NPC474690
0.7606	Intermediate Similarity	NPC97322
0.7606	Intermediate Similarity	NPC475795
0.759	Intermediate Similarity	NPC85774
0.759	Intermediate Similarity	NPC214043
0.7568	Intermediate Similarity	NPC4370
0.7568	Intermediate Similarity	NPC220210
0.7568	Intermediate Similarity	NPC20181
0.7568	Intermediate Similarity	NPC290350
0.7564	Intermediate Similarity	NPC65650
0.7561	Intermediate Similarity	NPC311092
0.7561	Intermediate Similarity	NPC327969
0.7561	Intermediate Similarity	NPC268122
0.7561	Intermediate Similarity	NPC321289
0.7561	Intermediate Similarity	NPC193347
0.7536	Intermediate Similarity	NPC49575
0.7536	Intermediate Similarity	NPC55004
0.7536	Intermediate Similarity	NPC267626
0.7532	Intermediate Similarity	NPC56747
0.7532	Intermediate Similarity	NPC109576
0.7532	Intermediate Similarity	NPC180015
0.7532	Intermediate Similarity	NPC130016
0.7532	Intermediate Similarity	NPC52667
0.7532	Intermediate Similarity	NPC474488
0.7531	Intermediate Similarity	NPC472478
0.7531	Intermediate Similarity	NPC287063

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 NPC474797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1499
0.2-0.3	4420
0.3-0.4	2245
0.4-0.5	450
0.5-0.6	163
0.6-0.7	149
0.7-0.8	58
0.8-0.85	2
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9429	High Similarity	NPD4058	Approved
0.9	High Similarity	NPD4691	Approved
0.8889	High Similarity	NPD5733	Approved
0.8889	High Similarity	NPD4687	Approved
0.8857	High Similarity	NPD4137	Phase 3
0.8732	High Similarity	NPD4747	Approved
0.8611	High Similarity	NPD5276	Approved
0.8194	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4221	Approved
0.7561	Intermediate Similarity	NPD4223	Phase 3
0.75	Intermediate Similarity	NPD5329	Approved
0.7442	Intermediate Similarity	NPD6672	Approved
0.7442	Intermediate Similarity	NPD5737	Approved
0.7412	Intermediate Similarity	NPD5280	Approved
0.7412	Intermediate Similarity	NPD7334	Approved
0.7412	Intermediate Similarity	NPD5690	Phase 2
0.7412	Intermediate Similarity	NPD6684	Approved
0.7412	Intermediate Similarity	NPD7521	Approved
0.7412	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7146	Approved
0.7412	Intermediate Similarity	NPD6409	Approved
0.7412	Intermediate Similarity	NPD5330	Approved
0.7412	Intermediate Similarity	NPD4694	Approved
0.7386	Intermediate Similarity	NPD5694	Approved
0.7386	Intermediate Similarity	NPD6050	Approved
0.7386	Intermediate Similarity	NPD5284	Approved
0.7386	Intermediate Similarity	NPD5281	Approved
0.7386	Intermediate Similarity	NPD6079	Approved
0.7381	Intermediate Similarity	NPD3133	Approved
0.7381	Intermediate Similarity	NPD3666	Approved
0.7381	Intermediate Similarity	NPD4197	Approved
0.7381	Intermediate Similarity	NPD3665	Phase 1
0.7356	Intermediate Similarity	NPD6904	Approved
0.7356	Intermediate Similarity	NPD6673	Approved
0.7356	Intermediate Similarity	NPD6080	Approved
0.7317	Intermediate Similarity	NPD4695	Discontinued
0.7284	Intermediate Similarity	NPD3617	Approved
0.7273	Intermediate Similarity	NPD5692	Phase 3
0.7273	Intermediate Similarity	NPD5207	Approved
0.7241	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6903	Approved
0.7229	Intermediate Similarity	NPD8028	Phase 2
0.7209	Intermediate Similarity	NPD4138	Approved
0.7209	Intermediate Similarity	NPD4689	Approved
0.7209	Intermediate Similarity	NPD5279	Phase 3
0.7209	Intermediate Similarity	NPD4690	Approved
0.7209	Intermediate Similarity	NPD5205	Approved
0.7209	Intermediate Similarity	NPD4688	Approved
0.7209	Intermediate Similarity	NPD4693	Phase 3
0.7209	Intermediate Similarity	NPD3618	Phase 1
0.7195	Intermediate Similarity	NPD4195	Approved
0.7183	Intermediate Similarity	NPD287	Approved
0.7176	Intermediate Similarity	NPD4786	Approved
0.7176	Intermediate Similarity	NPD3668	Phase 3
0.7159	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5222	Approved
0.7065	Intermediate Similarity	NPD5221	Approved
0.7045	Intermediate Similarity	NPD5208	Approved
0.7011	Intermediate Similarity	NPD4519	Discontinued
0.7011	Intermediate Similarity	NPD4623	Approved
0.7011	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD5693	Phase 1
0.6989	Remote Similarity	NPD5173	Approved
0.6966	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3573	Approved
0.6889	Remote Similarity	NPD4096	Approved
0.686	Remote Similarity	NPD4788	Approved
0.6854	Remote Similarity	NPD4518	Approved
0.6842	Remote Similarity	NPD5285	Approved
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6809	Remote Similarity	NPD6083	Phase 2
0.6809	Remote Similarity	NPD6084	Phase 2
0.6774	Remote Similarity	NPD5654	Approved
0.6771	Remote Similarity	NPD5223	Approved
0.6739	Remote Similarity	NPD6399	Phase 3
0.6739	Remote Similarity	NPD5133	Approved
0.6739	Remote Similarity	NPD4202	Approved
0.6706	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4697	Phase 3
0.6701	Remote Similarity	NPD5226	Approved
0.6701	Remote Similarity	NPD4633	Approved
0.6701	Remote Similarity	NPD5091	Approved
0.6701	Remote Similarity	NPD5225	Approved
0.6701	Remote Similarity	NPD5211	Phase 2
0.6701	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6633	Remote Similarity	NPD5174	Approved
0.6633	Remote Similarity	NPD5175	Approved
0.6632	Remote Similarity	NPD4755	Approved
0.6632	Remote Similarity	NPD3495	Discontinued
0.6632	Remote Similarity	NPD5959	Approved
0.663	Remote Similarity	NPD7515	Phase 2
0.6625	Remote Similarity	NPD7143	Approved
0.6625	Remote Similarity	NPD7144	Approved
0.66	Remote Similarity	NPD6614	Approved
0.6596	Remote Similarity	NPD5695	Phase 3
0.6566	Remote Similarity	NPD5141	Approved
0.6562	Remote Similarity	NPD5696	Approved
0.6559	Remote Similarity	NPD7631	Approved
0.6543	Remote Similarity	NPD7151	Approved
0.6543	Remote Similarity	NPD7152	Approved
0.6543	Remote Similarity	NPD7150	Approved
0.6535	Remote Similarity	NPD6899	Approved
0.6535	Remote Similarity	NPD6881	Approved
0.65	Remote Similarity	NPD6922	Approved
0.65	Remote Similarity	NPD6923	Approved
0.6495	Remote Similarity	NPD4700	Approved
0.6495	Remote Similarity	NPD6404	Discontinued
0.6489	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6052	Approved
0.6452	Remote Similarity	NPD7609	Phase 3
0.6437	Remote Similarity	NPD4692	Approved
0.6437	Remote Similarity	NPD4139	Approved
0.6436	Remote Similarity	NPD5697	Approved
0.6408	Remote Similarity	NPD7102	Approved
0.6408	Remote Similarity	NPD6883	Approved
0.6408	Remote Similarity	NPD7290	Approved
0.6386	Remote Similarity	NPD6924	Approved
0.6386	Remote Similarity	NPD4784	Approved
0.6386	Remote Similarity	NPD4785	Approved
0.6386	Remote Similarity	NPD6926	Approved
0.6373	Remote Similarity	NPD5168	Approved
0.6373	Remote Similarity	NPD6011	Approved
0.6373	Remote Similarity	NPD4730	Approved
0.6373	Remote Similarity	NPD4729	Approved
0.6354	Remote Similarity	NPD7732	Phase 3
0.6354	Remote Similarity	NPD7614	Phase 1
0.6353	Remote Similarity	NPD6932	Approved
0.6346	Remote Similarity	NPD6847	Approved
0.6346	Remote Similarity	NPD8130	Phase 1
0.6346	Remote Similarity	NPD6649	Approved
0.6346	Remote Similarity	NPD6617	Approved
0.6346	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD6869	Approved
0.6341	Remote Similarity	NPD4243	Approved
0.6337	Remote Similarity	NPD6675	Approved
0.6337	Remote Similarity	NPD7128	Approved
0.6337	Remote Similarity	NPD5739	Approved
0.6337	Remote Similarity	NPD6402	Approved
0.6333	Remote Similarity	NPD1694	Approved
0.6329	Remote Similarity	NPD7331	Phase 2
0.6316	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.63	Remote Similarity	NPD4754	Approved
0.6289	Remote Similarity	NPD7902	Approved
0.6286	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD8297	Approved
0.6279	Remote Similarity	NPD7145	Approved
0.6277	Remote Similarity	NPD7637	Suspended
0.6275	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6933	Approved
0.6234	Remote Similarity	NPD4193	Approved
0.6234	Remote Similarity	NPD4192	Approved
0.6234	Remote Similarity	NPD4191	Approved
0.6234	Remote Similarity	NPD4194	Approved
0.6226	Remote Similarity	NPD6858	Approved
0.6226	Remote Similarity	NPD7094	Approved
0.6224	Remote Similarity	NPD7638	Approved
0.6214	Remote Similarity	NPD7320	Approved
0.6214	Remote Similarity	NPD5128	Approved
0.6211	Remote Similarity	NPD1508	Approved
0.619	Remote Similarity	NPD5127	Approved
0.619	Remote Similarity	NPD5217	Approved
0.619	Remote Similarity	NPD5216	Approved
0.619	Remote Similarity	NPD5215	Approved
0.618	Remote Similarity	NPD5209	Approved
0.6176	Remote Similarity	NPD4768	Approved
0.6176	Remote Similarity	NPD6008	Approved
0.6176	Remote Similarity	NPD4767	Approved
0.617	Remote Similarity	NPD5785	Approved
0.6163	Remote Similarity	NPD5776	Phase 2
0.6163	Remote Similarity	NPD6925	Approved
0.6162	Remote Similarity	NPD7639	Approved
0.6162	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6372	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