NPASS Compound

Structure

CID176107 OpenBabel06191715552D 28 31 0 0 1 0 0 0 0 0999 V2000 -3.9926 6.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5325 5.6891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8042 3.7080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5322 2.4699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7403 3.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1684 4.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3441 3.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8434 -1.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6874 -0.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2183 1.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2180 0.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8431 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6882 1.9476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5645 5.5876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3761 2.9204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6867 -0.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3758 1.9471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5316 0.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8440 0.4869 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 -2.5319 1.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5529 -1.4736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 28 2 0 0 0 0 22 10 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 27 1 6 0 0 0 24 27 1 6 0 0 0 25 26 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.31
Volume:	439.567
LogP:	7.176
LogD:	6.117
LogS:	-6.513
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	4.591
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.54
MDCK Permeability:	2.6338402676628903e-05
Pgp-inhibitor:	0.201
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.459
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	94.81700897216797%
Volume Distribution (VD):	2.195
Pgp-substrate:	2.9005846977233887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.313
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.899
CYP2C19-substrate:	0.774
CYP2C9-inhibitor:	0.814
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.777
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	3.612
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.518
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.396
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.966
Carcinogencity:	0.401
Eye Corrosion:	0.806
Eye Irritation:	0.609
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC176107

Natural Product ID:	NPC176107
*Common Name:**	Dendronesterone C
IUPAC Name:	(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-6-methylhept-3-en-2-yl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Dendronesterone C
Standard InCHIKey:	AJWONNNXQUONDT-UAJHHUEASA-N
Standard InCHI:	InChI=1S/C27H40O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6,8,13,15,17-19,22-25H,7,9-12,14,16H2,1-5H3/b8-6+/t19-,22+,23-,24+,25+,26+,27-/m1/s1
SMILES:	CC(C/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457600
PubChem CID:	11176468
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO33357	lemnalia carvicorni	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO14183	Dendronephthya studeri	Species	Nephtheidae	Eukaryota	n.a.	at a depth of 20 m, the coast of Xiaodong Sea, Hainan Province, China	2001-DEC	PMID[21192715]
NPO14183	Dendronephthya studeri	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21192715]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14183	Dendronephthya studeri	Species	Nephtheidae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	100.0	uM	PMID[516382]
NPT168	Cell Line	P388	Mus musculus	ED50	>	100.0	uM	PMID[516382]

☑ 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 NPC176107 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	176
0.1-0.2	2288
0.2-0.3	15756
0.3-0.4	10929
0.4-0.5	7282
0.5-0.6	4600
0.6-0.7	1385
0.7-0.8	239
0.8-0.85	9
0.85-0.9	25
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC92327
0.9254	High Similarity	NPC251705
0.9219	High Similarity	NPC176171
0.9104	High Similarity	NPC234707
0.9104	High Similarity	NPC115023
0.8986	High Similarity	NPC293803
0.8971	High Similarity	NPC470044
0.8971	High Similarity	NPC303613
0.8971	High Similarity	NPC470045
0.8971	High Similarity	NPC474228
0.8955	High Similarity	NPC282593
0.8955	High Similarity	NPC159577
0.8955	High Similarity	NPC35734
0.8857	High Similarity	NPC69408
0.8857	High Similarity	NPC474463
0.8841	High Similarity	NPC309852
0.8824	High Similarity	NPC305501
0.8824	High Similarity	NPC54123
0.8806	High Similarity	NPC182815
0.871	High Similarity	NPC60772
0.8676	High Similarity	NPC265782
0.8676	High Similarity	NPC307176
0.8676	High Similarity	NPC251929
0.8676	High Similarity	NPC2634
0.8657	High Similarity	NPC20610
0.8611	High Similarity	NPC105197
0.8571	High Similarity	NPC255021
0.8551	High Similarity	NPC470078
0.8529	High Similarity	NPC139397
0.8493	Intermediate Similarity	NPC190211
0.8451	Intermediate Similarity	NPC255650
0.8406	Intermediate Similarity	NPC260040
0.8378	Intermediate Similarity	NPC474509
0.8358	Intermediate Similarity	NPC323005
0.831	Intermediate Similarity	NPC329866
0.831	Intermediate Similarity	NPC474796
0.831	Intermediate Similarity	NPC474797
0.8194	Intermediate Similarity	NPC473171
0.8143	Intermediate Similarity	NPC40574
0.8143	Intermediate Similarity	NPC477856
0.8143	Intermediate Similarity	NPC214770
0.8116	Intermediate Similarity	NPC188292
0.8116	Intermediate Similarity	NPC260474
0.8065	Intermediate Similarity	NPC5626
0.806	Intermediate Similarity	NPC469662
0.8028	Intermediate Similarity	NPC5701
0.8028	Intermediate Similarity	NPC225467
0.8	Intermediate Similarity	NPC170793
0.8	Intermediate Similarity	NPC90965
0.8	Intermediate Similarity	NPC256846
0.7949	Intermediate Similarity	NPC33913
0.7922	Intermediate Similarity	NPC472239
0.791	Intermediate Similarity	NPC165695
0.791	Intermediate Similarity	NPC202118
0.791	Intermediate Similarity	NPC197238
0.7903	Intermediate Similarity	NPC14002
0.7887	Intermediate Similarity	NPC475728
0.7867	Intermediate Similarity	NPC82635
0.7867	Intermediate Similarity	NPC470052
0.7857	Intermediate Similarity	NPC87141
0.7857	Intermediate Similarity	NPC310992
0.7848	Intermediate Similarity	NPC29447
0.7846	Intermediate Similarity	NPC469769
0.7838	Intermediate Similarity	NPC469796
0.7838	Intermediate Similarity	NPC469793
0.7794	Intermediate Similarity	NPC212210
0.7792	Intermediate Similarity	NPC6434
0.7778	Intermediate Similarity	NPC223187
0.7778	Intermediate Similarity	NPC181204
0.7778	Intermediate Similarity	NPC190035
0.7761	Intermediate Similarity	NPC213152
0.7746	Intermediate Similarity	NPC477857
0.7733	Intermediate Similarity	NPC91665
0.7722	Intermediate Similarity	NPC472265
0.7692	Intermediate Similarity	NPC3511
0.7692	Intermediate Similarity	NPC472867
0.7692	Intermediate Similarity	NPC142253
0.7692	Intermediate Similarity	NPC100297
0.7692	Intermediate Similarity	NPC320514
0.7681	Intermediate Similarity	NPC251118
0.7656	Intermediate Similarity	NPC123194
0.7654	Intermediate Similarity	NPC93778
0.7632	Intermediate Similarity	NPC469996
0.7619	Intermediate Similarity	NPC23117
0.7612	Intermediate Similarity	NPC25853
0.7612	Intermediate Similarity	NPC127582
0.7606	Intermediate Similarity	NPC142754
0.7606	Intermediate Similarity	NPC39157
0.7606	Intermediate Similarity	NPC82477
0.7606	Intermediate Similarity	NPC296697
0.7571	Intermediate Similarity	NPC43300
0.7571	Intermediate Similarity	NPC107704
0.7571	Intermediate Similarity	NPC96812
0.7571	Intermediate Similarity	NPC189917
0.7571	Intermediate Similarity	NPC168824
0.7571	Intermediate Similarity	NPC39462
0.7536	Intermediate Similarity	NPC475124
0.7536	Intermediate Similarity	NPC285371
0.75	Intermediate Similarity	NPC214043
0.75	Intermediate Similarity	NPC181743
0.75	Intermediate Similarity	NPC470557
0.75	Intermediate Similarity	NPC286814
0.75	Intermediate Similarity	NPC16287
0.75	Intermediate Similarity	NPC87552
0.75	Intermediate Similarity	NPC178025
0.75	Intermediate Similarity	NPC85774
0.747	Intermediate Similarity	NPC177141
0.747	Intermediate Similarity	NPC262043
0.7468	Intermediate Similarity	NPC193347
0.7468	Intermediate Similarity	NPC469805
0.7468	Intermediate Similarity	NPC469804
0.7465	Intermediate Similarity	NPC220210
0.7465	Intermediate Similarity	NPC475523
0.7465	Intermediate Similarity	NPC20181
0.7463	Intermediate Similarity	NPC276764
0.7463	Intermediate Similarity	NPC472304
0.7439	Intermediate Similarity	NPC476293
0.7439	Intermediate Similarity	NPC58063
0.7436	Intermediate Similarity	NPC472478
0.7407	Intermediate Similarity	NPC8571
0.7407	Intermediate Similarity	NPC469948
0.7407	Intermediate Similarity	NPC60350
0.7407	Intermediate Similarity	NPC22133
0.7403	Intermediate Similarity	NPC228911
0.7403	Intermediate Similarity	NPC115515
0.7391	Intermediate Similarity	NPC472306
0.7391	Intermediate Similarity	NPC288253
0.7381	Intermediate Similarity	NPC273199
0.7375	Intermediate Similarity	NPC41539
0.7375	Intermediate Similarity	NPC474976
0.7375	Intermediate Similarity	NPC3856
0.7375	Intermediate Similarity	NPC474790
0.7375	Intermediate Similarity	NPC279639
0.7368	Intermediate Similarity	NPC113733
0.7368	Intermediate Similarity	NPC129165
0.7368	Intermediate Similarity	NPC134330
0.7368	Intermediate Similarity	NPC292589
0.7368	Intermediate Similarity	NPC1254
0.7368	Intermediate Similarity	NPC112680
0.7361	Intermediate Similarity	NPC155198
0.7344	Intermediate Similarity	NPC69898
0.7344	Intermediate Similarity	NPC295777
0.7342	Intermediate Similarity	NPC147066
0.7342	Intermediate Similarity	NPC477372
0.7333	Intermediate Similarity	NPC159497
0.7333	Intermediate Similarity	NPC128346
0.7333	Intermediate Similarity	NPC219232
0.7333	Intermediate Similarity	NPC211641
0.7324	Intermediate Similarity	NPC259156
0.7324	Intermediate Similarity	NPC242945
0.7317	Intermediate Similarity	NPC474732
0.7317	Intermediate Similarity	NPC145879
0.7317	Intermediate Similarity	NPC474778
0.7317	Intermediate Similarity	NPC474733
0.7317	Intermediate Similarity	NPC475022
0.7317	Intermediate Similarity	NPC118648
0.7317	Intermediate Similarity	NPC222613
0.7317	Intermediate Similarity	NPC31564
0.7313	Intermediate Similarity	NPC266295
0.7313	Intermediate Similarity	NPC30215
0.7313	Intermediate Similarity	NPC311852
0.7313	Intermediate Similarity	NPC94991
0.7313	Intermediate Similarity	NPC27610
0.7313	Intermediate Similarity	NPC56905
0.7308	Intermediate Similarity	NPC153987
0.7308	Intermediate Similarity	NPC215843
0.7308	Intermediate Similarity	NPC44083
0.7294	Intermediate Similarity	NPC218301
0.7294	Intermediate Similarity	NPC272746
0.7286	Intermediate Similarity	NPC52449
0.7286	Intermediate Similarity	NPC169275
0.7284	Intermediate Similarity	NPC473246
0.7284	Intermediate Similarity	NPC237712
0.7284	Intermediate Similarity	NPC144258
0.7258	Intermediate Similarity	NPC22765
0.7258	Intermediate Similarity	NPC17518
0.725	Intermediate Similarity	NPC469806
0.725	Intermediate Similarity	NPC469799
0.725	Intermediate Similarity	NPC321289
0.725	Intermediate Similarity	NPC327969
0.7246	Intermediate Similarity	NPC60565
0.7237	Intermediate Similarity	NPC141071
0.7237	Intermediate Similarity	NPC476346
0.7237	Intermediate Similarity	NPC136188
0.7237	Intermediate Similarity	NPC230301
0.7237	Intermediate Similarity	NPC22105
0.7237	Intermediate Similarity	NPC28657
0.7237	Intermediate Similarity	NPC471723
0.7237	Intermediate Similarity	NPC134847
0.7237	Intermediate Similarity	NPC257347
0.7237	Intermediate Similarity	NPC304309
0.7237	Intermediate Similarity	NPC285893
0.7237	Intermediate Similarity	NPC162742
0.7237	Intermediate Similarity	NPC288035
0.7229	Intermediate Similarity	NPC475740
0.7229	Intermediate Similarity	NPC75315
0.7229	Intermediate Similarity	NPC136948
0.7229	Intermediate Similarity	NPC163016
0.7215	Intermediate Similarity	NPC469798
0.7215	Intermediate Similarity	NPC476809

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 NPC176107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2165
0.2-0.3	4896
0.3-0.4	1364
0.4-0.5	247
0.5-0.6	125
0.6-0.7	128
0.7-0.8	49
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8676	High Similarity	NPD4691	Approved
0.8676	High Similarity	NPD4747	Approved
0.8571	High Similarity	NPD4058	Approved
0.8529	High Similarity	NPD4137	Phase 3
0.831	Intermediate Similarity	NPD4687	Approved
0.831	Intermediate Similarity	NPD5733	Approved
0.8243	Intermediate Similarity	NPD4195	Approved
0.8116	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD5276	Approved
0.7568	Intermediate Similarity	NPD4784	Approved
0.7568	Intermediate Similarity	NPD4785	Approved
0.7534	Intermediate Similarity	NPD4243	Approved
0.7468	Intermediate Similarity	NPD4223	Phase 3
0.7468	Intermediate Similarity	NPD4221	Approved
0.7407	Intermediate Similarity	NPD5329	Approved
0.7375	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5690	Phase 2
0.7294	Intermediate Similarity	NPD6079	Approved
0.7284	Intermediate Similarity	NPD4197	Approved
0.7237	Intermediate Similarity	NPD6942	Approved
0.7237	Intermediate Similarity	NPD7339	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7108	Intermediate Similarity	NPD4689	Approved
0.7108	Intermediate Similarity	NPD6409	Approved
0.7108	Intermediate Similarity	NPD6684	Approved
0.7108	Intermediate Similarity	NPD7146	Approved
0.7108	Intermediate Similarity	NPD4688	Approved
0.7108	Intermediate Similarity	NPD4138	Approved
0.7108	Intermediate Similarity	NPD7521	Approved
0.7108	Intermediate Similarity	NPD5330	Approved
0.7108	Intermediate Similarity	NPD5205	Approved
0.7108	Intermediate Similarity	NPD4693	Phase 3
0.7108	Intermediate Similarity	NPD7334	Approved
0.7108	Intermediate Similarity	NPD4690	Approved
0.7073	Intermediate Similarity	NPD4786	Approved
0.7073	Intermediate Similarity	NPD3133	Approved
0.7073	Intermediate Similarity	NPD3666	Approved
0.7073	Intermediate Similarity	NPD3665	Phase 1
0.7059	Intermediate Similarity	NPD6904	Approved
0.7059	Intermediate Similarity	NPD6673	Approved
0.7059	Intermediate Similarity	NPD6080	Approved
0.7059	Intermediate Similarity	NPD287	Approved
0.7059	Intermediate Similarity	NPD5328	Approved
0.7013	Intermediate Similarity	NPD5275	Approved
0.7013	Intermediate Similarity	NPD4190	Phase 3
0.6962	Remote Similarity	NPD3617	Approved
0.6941	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5208	Approved
0.6941	Remote Similarity	NPD6903	Approved
0.6933	Remote Similarity	NPD6939	Phase 2
0.6933	Remote Similarity	NPD7143	Approved
0.6933	Remote Similarity	NPD7144	Approved
0.6933	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8028	Phase 2
0.6905	Remote Similarity	NPD3618	Phase 1
0.6905	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6098	Approved
0.6905	Remote Similarity	NPD5280	Approved
0.6905	Remote Similarity	NPD4694	Approved
0.686	Remote Similarity	NPD4753	Phase 2
0.6854	Remote Similarity	NPD5210	Approved
0.6854	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD7150	Approved
0.6842	Remote Similarity	NPD7151	Approved
0.6842	Remote Similarity	NPD7152	Approved
0.6829	Remote Similarity	NPD3667	Approved
0.68	Remote Similarity	NPD6922	Approved
0.68	Remote Similarity	NPD6923	Approved
0.679	Remote Similarity	NPD4695	Discontinued
0.6782	Remote Similarity	NPD5207	Approved
0.6778	Remote Similarity	NPD5222	Approved
0.6778	Remote Similarity	NPD5221	Approved
0.6778	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4623	Approved
0.6706	Remote Similarity	NPD5279	Phase 3
0.6706	Remote Similarity	NPD4519	Discontinued
0.6705	Remote Similarity	NPD5694	Approved
0.6705	Remote Similarity	NPD5284	Approved
0.6705	Remote Similarity	NPD5281	Approved
0.6705	Remote Similarity	NPD5693	Phase 1
0.6705	Remote Similarity	NPD6050	Approved
0.6703	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4202	Approved
0.6628	Remote Similarity	NPD3573	Approved
0.6591	Remote Similarity	NPD5692	Phase 3
0.6585	Remote Similarity	NPD7525	Registered
0.6559	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD5286	Approved
0.6559	Remote Similarity	NPD5285	Approved
0.6556	Remote Similarity	NPD6001	Approved
0.6548	Remote Similarity	NPD4788	Approved
0.6522	Remote Similarity	NPD6084	Phase 2
0.6522	Remote Similarity	NPD6083	Phase 2
0.6489	Remote Similarity	NPD5223	Approved
0.6477	Remote Similarity	NPD6051	Approved
0.6456	Remote Similarity	NPD6926	Approved
0.6456	Remote Similarity	NPD6924	Approved
0.6452	Remote Similarity	NPD5290	Discontinued
0.6444	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD5226	Approved
0.6421	Remote Similarity	NPD5211	Phase 2
0.6421	Remote Similarity	NPD4633	Approved
0.6421	Remote Similarity	NPD5225	Approved
0.6421	Remote Similarity	NPD5091	Approved
0.6421	Remote Similarity	NPD5224	Approved
0.642	Remote Similarity	NPD6932	Approved
0.6413	Remote Similarity	NPD4697	Phase 3
0.6404	Remote Similarity	NPD4096	Approved
0.6364	Remote Similarity	NPD4518	Approved
0.6354	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD5175	Approved
0.6344	Remote Similarity	NPD4755	Approved
0.6341	Remote Similarity	NPD7145	Approved
0.6327	Remote Similarity	NPD6614	Approved
0.631	Remote Similarity	NPD4139	Approved
0.631	Remote Similarity	NPD4692	Approved
0.6304	Remote Similarity	NPD5695	Phase 3
0.6301	Remote Similarity	NPD4194	Approved
0.6301	Remote Similarity	NPD4191	Approved
0.6301	Remote Similarity	NPD4192	Approved
0.6301	Remote Similarity	NPD4193	Approved
0.6296	Remote Similarity	NPD6933	Approved
0.629	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5141	Approved
0.6277	Remote Similarity	NPD5696	Approved
0.6264	Remote Similarity	NPD5133	Approved
0.6263	Remote Similarity	NPD6899	Approved
0.6263	Remote Similarity	NPD6881	Approved
0.622	Remote Similarity	NPD6925	Approved
0.622	Remote Similarity	NPD5776	Phase 2
0.6212	Remote Similarity	NPD8262	Approved
0.6211	Remote Similarity	NPD4700	Approved
0.619	Remote Similarity	NPD7514	Phase 3
0.6186	Remote Similarity	NPD6052	Approved
0.6162	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.6145	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD6883	Approved
0.6139	Remote Similarity	NPD7290	Approved
0.6129	Remote Similarity	NPD5654	Approved
0.6118	Remote Similarity	NPD6902	Approved
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4729	Approved
0.61	Remote Similarity	NPD4730	Approved
0.61	Remote Similarity	NPD6011	Approved
0.61	Remote Similarity	NPD5168	Approved
0.6078	Remote Similarity	NPD6650	Approved
0.6078	Remote Similarity	NPD8130	Phase 1
0.6078	Remote Similarity	NPD6649	Approved
0.6078	Remote Similarity	NPD6869	Approved
0.6078	Remote Similarity	NPD6847	Approved
0.6078	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD7645	Phase 2
0.6071	Remote Similarity	NPD6929	Approved
0.6071	Remote Similarity	NPD6683	Phase 2
0.6067	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7128	Approved
0.6061	Remote Similarity	NPD5739	Approved
0.6061	Remote Similarity	NPD6675	Approved
0.6061	Remote Similarity	NPD6402	Approved
0.6047	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6404	Discontinued
0.604	Remote Similarity	NPD6013	Approved
0.604	Remote Similarity	NPD6014	Approved
0.604	Remote Similarity	NPD6012	Approved
0.6022	Remote Similarity	NPD7900	Approved
0.6022	Remote Similarity	NPD5707	Approved
0.6022	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7748	Approved
0.6022	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4754	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6	Remote Similarity	NPD3495	Discontinued
0.6	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD4723	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD4722	Approved
0.6	Remote Similarity	NPD6931	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.598	Remote Similarity	NPD5169	Approved
0.598	Remote Similarity	NPD5247	Approved
0.598	Remote Similarity	NPD5251	Approved
0.598	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5250	Approved
0.598	Remote Similarity	NPD5135	Approved
0.598	Remote Similarity	NPD5248	Approved
0.598	Remote Similarity	NPD5249	Phase 3
0.598	Remote Similarity	NPD4634	Approved
0.5941	Remote Similarity	NPD5128	Approved
0.5941	Remote Similarity	NPD7320	Approved
0.5938	Remote Similarity	NPD7638	Approved
0.5922	Remote Similarity	NPD5217	Approved
0.5922	Remote Similarity	NPD5216	Approved
0.5922	Remote Similarity	NPD5215	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