NPASS Compound

Structure

NPC136801 OpenBabel07101718202D 36 39 0 0 1 0 0 0 0 0999 V2000 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1456 1.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9377 2.5529 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 -0.4067 -1.9135 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 2.2382 1.4680 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 2.4190 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 0.9511 -1.3090 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 -3.4641 -1.0000 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 1.2601 1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5254 2.6270 0.0000 C 0 0 2 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 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 0.9000 2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 3.5780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8855 0.9328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 11 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 18 30 1 1 0 0 0 19 20 2 0 0 0 0 19 29 1 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 27 1 0 0 0 0 23 33 1 1 0 0 0 24 30 1 0 0 0 0 24 34 2 0 0 0 0 25 26 1 0 0 0 0 25 35 1 1 0 0 0 27 36 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.36
Volume:	540.679
LogP:	3.07
LogD:	2.426
LogS:	-3.597
# Rotatable Bonds:	6
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.35
Synthetic Accessibility Score:	5.344
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.269
MDCK Permeability:	3.889043455274077e-06
Pgp-inhibitor:	0.138
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.237
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	81.2259521484375%
Volume Distribution (VD):	0.674
Pgp-substrate:	7.289759635925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.64
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.147
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	3.291
Half-life (T1/2):	0.668

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.279
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.803
Carcinogencity:	0.01
Eye Corrosion:	0.037
Eye Irritation:	0.116
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC136801

Natural Product ID:	NPC136801
*Common Name:**	Fasciculol I
IUPAC Name:	(2R,3R,5R,10S,13R,14S,17R)-2,3-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2R,5R)-1,5,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,5,6,7,11,15,16,17-decahydrocyclopenta[a]phenanthren-12-one
Synonyms:
Standard InCHIKey:	MNTGMRBOSQJGGX-ULBHAVAUSA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-26(2)22-10-9-19-20(28(22,5)15-21(32)25(26)35)14-24(34)30(7)18(12-13-29(19,30)6)17(16-31)8-11-23(33)27(3,4)36/h17-18,21-23,25,31-33,35-36H,8-16H2,1-7H3/t17-,18+,21+,22-,23+,25-,28+,29-,30-/m0/s1
SMILES:	OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)C(=O)CC1=C2CC[C@@H]2[C@]1(C)C[C@@H](O)[C@@H](C2(C)C)O)C)CC[C@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375643
PubChem CID:	72714437
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
NPO33351	naematoloma fasciculare	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23634786]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	30000.0	nM	PMID[491480]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[491480]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[491480]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	7980.0	nM	PMID[491480]

☑ 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 NPC136801 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	186
0.1-0.2	1518
0.2-0.3	5520
0.3-0.4	14559
0.4-0.5	7882
0.5-0.6	6067
0.6-0.7	5539
0.7-0.8	1259
0.8-0.85	143
0.85-0.9	19
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC138756
0.9545	High Similarity	NPC200702
0.9091	High Similarity	NPC289213
0.8824	High Similarity	NPC7988
0.8764	High Similarity	NPC32830
0.875	High Similarity	NPC99909
0.8723	High Similarity	NPC316964
0.866	High Similarity	NPC323834
0.8652	High Similarity	NPC131470
0.8652	High Similarity	NPC193360
0.8652	High Similarity	NPC143767
0.8652	High Similarity	NPC44181
0.8646	High Similarity	NPC191892
0.8636	High Similarity	NPC72133
0.8636	High Similarity	NPC89077
0.8588	High Similarity	NPC22403
0.8571	High Similarity	NPC233116
0.8571	High Similarity	NPC189520
0.8557	High Similarity	NPC209502
0.8557	High Similarity	NPC204833
0.8556	High Similarity	NPC275740
0.8556	High Similarity	NPC86319
0.8556	High Similarity	NPC250592
0.8556	High Similarity	NPC77263
0.8539	High Similarity	NPC241875
0.8539	High Similarity	NPC90652
0.8539	High Similarity	NPC469314
0.8539	High Similarity	NPC469317
0.8495	Intermediate Similarity	NPC48330
0.8495	Intermediate Similarity	NPC127063
0.8495	Intermediate Similarity	NPC297199
0.8469	Intermediate Similarity	NPC48733
0.8469	Intermediate Similarity	NPC202167
0.8469	Intermediate Similarity	NPC149047
0.8469	Intermediate Similarity	NPC171137
0.8469	Intermediate Similarity	NPC152695
0.8469	Intermediate Similarity	NPC296945
0.8469	Intermediate Similarity	NPC260268
0.8469	Intermediate Similarity	NPC476027
0.8469	Intermediate Similarity	NPC85829
0.8469	Intermediate Similarity	NPC302607
0.8469	Intermediate Similarity	NPC319077
0.8469	Intermediate Similarity	NPC97202
0.8469	Intermediate Similarity	NPC214264
0.8469	Intermediate Similarity	NPC150531
0.8469	Intermediate Similarity	NPC50692
0.8469	Intermediate Similarity	NPC49958
0.8462	Intermediate Similarity	NPC469400
0.8462	Intermediate Similarity	NPC183283
0.8444	Intermediate Similarity	NPC471724
0.8444	Intermediate Similarity	NPC470417
0.8444	Intermediate Similarity	NPC471722
0.8444	Intermediate Similarity	NPC242864
0.8427	Intermediate Similarity	NPC94755
0.8427	Intermediate Similarity	NPC55309
0.8427	Intermediate Similarity	NPC28252
0.8404	Intermediate Similarity	NPC249954
0.8404	Intermediate Similarity	NPC173272
0.8404	Intermediate Similarity	NPC7124
0.8387	Intermediate Similarity	NPC111015
0.8387	Intermediate Similarity	NPC196485
0.8387	Intermediate Similarity	NPC245972
0.8387	Intermediate Similarity	NPC166906
0.8384	Intermediate Similarity	NPC475060
0.8384	Intermediate Similarity	NPC83744
0.8384	Intermediate Similarity	NPC165873
0.8384	Intermediate Similarity	NPC477916
0.8384	Intermediate Similarity	NPC220229
0.837	Intermediate Similarity	NPC63748
0.837	Intermediate Similarity	NPC155304
0.8352	Intermediate Similarity	NPC474245
0.8352	Intermediate Similarity	NPC186688
0.8351	Intermediate Similarity	NPC473424
0.8351	Intermediate Similarity	NPC477915
0.8333	Intermediate Similarity	NPC187376
0.8333	Intermediate Similarity	NPC159046
0.8333	Intermediate Similarity	NPC110149
0.8333	Intermediate Similarity	NPC233836
0.8316	Intermediate Similarity	NPC122294
0.8316	Intermediate Similarity	NPC320306
0.8316	Intermediate Similarity	NPC170978
0.8316	Intermediate Similarity	NPC190554
0.8315	Intermediate Similarity	NPC197823
0.83	Intermediate Similarity	NPC65941
0.83	Intermediate Similarity	NPC217201
0.83	Intermediate Similarity	NPC329417
0.8298	Intermediate Similarity	NPC271195
0.8298	Intermediate Similarity	NPC255809
0.8298	Intermediate Similarity	NPC317586
0.8298	Intermediate Similarity	NPC473170
0.8298	Intermediate Similarity	NPC472485
0.8298	Intermediate Similarity	NPC259286
0.8298	Intermediate Similarity	NPC470016
0.8295	Intermediate Similarity	NPC86370
0.8283	Intermediate Similarity	NPC166607
0.828	Intermediate Similarity	NPC206810
0.828	Intermediate Similarity	NPC69454
0.8265	Intermediate Similarity	NPC55954
0.8265	Intermediate Similarity	NPC218513
0.8261	Intermediate Similarity	NPC191684
0.8261	Intermediate Similarity	NPC20388
0.8242	Intermediate Similarity	NPC280556
0.8242	Intermediate Similarity	NPC328539
0.8242	Intermediate Similarity	NPC53911
0.8229	Intermediate Similarity	NPC16021
0.8222	Intermediate Similarity	NPC472494
0.8222	Intermediate Similarity	NPC473168
0.8222	Intermediate Similarity	NPC472491
0.8218	Intermediate Similarity	NPC11710
0.8211	Intermediate Similarity	NPC305483
0.8211	Intermediate Similarity	NPC49371
0.8211	Intermediate Similarity	NPC95565
0.8211	Intermediate Similarity	NPC328162
0.8211	Intermediate Similarity	NPC96859
0.8202	Intermediate Similarity	NPC221758
0.8202	Intermediate Similarity	NPC59453
0.8202	Intermediate Similarity	NPC473246
0.8191	Intermediate Similarity	NPC318332
0.8182	Intermediate Similarity	NPC160843
0.8182	Intermediate Similarity	NPC471293
0.8182	Intermediate Similarity	NPC477812
0.8172	Intermediate Similarity	NPC297265
0.8172	Intermediate Similarity	NPC473166
0.8172	Intermediate Similarity	NPC73457
0.8172	Intermediate Similarity	NPC168027
0.8172	Intermediate Similarity	NPC185936
0.8172	Intermediate Similarity	NPC23434
0.8172	Intermediate Similarity	NPC107690
0.8172	Intermediate Similarity	NPC19114
0.8163	Intermediate Similarity	NPC296879
0.8163	Intermediate Similarity	NPC471119
0.8152	Intermediate Similarity	NPC229871
0.8152	Intermediate Similarity	NPC469319
0.8152	Intermediate Similarity	NPC474889
0.8152	Intermediate Similarity	NPC84271
0.8152	Intermediate Similarity	NPC1015
0.8152	Intermediate Similarity	NPC102414
0.8152	Intermediate Similarity	NPC475921
0.8152	Intermediate Similarity	NPC31985
0.8152	Intermediate Similarity	NPC77168
0.8152	Intermediate Similarity	NPC474704
0.8144	Intermediate Similarity	NPC144660
0.8144	Intermediate Similarity	NPC327431
0.8144	Intermediate Similarity	NPC307954
0.8144	Intermediate Similarity	NPC15390
0.8144	Intermediate Similarity	NPC83709
0.8144	Intermediate Similarity	NPC299971
0.8144	Intermediate Similarity	NPC154072
0.8137	Intermediate Similarity	NPC76084
0.8132	Intermediate Similarity	NPC474684
0.8132	Intermediate Similarity	NPC142361
0.8132	Intermediate Similarity	NPC475740
0.8125	Intermediate Similarity	NPC108078
0.8111	Intermediate Similarity	NPC474083
0.8111	Intermediate Similarity	NPC478127
0.8111	Intermediate Similarity	NPC470574
0.8105	Intermediate Similarity	NPC279974
0.8105	Intermediate Similarity	NPC472824
0.809	Intermediate Similarity	NPC278648
0.809	Intermediate Similarity	NPC476082
0.8085	Intermediate Similarity	NPC477855
0.8085	Intermediate Similarity	NPC470254
0.8085	Intermediate Similarity	NPC475255
0.8085	Intermediate Similarity	NPC274046
0.8085	Intermediate Similarity	NPC198074
0.8085	Intermediate Similarity	NPC291373
0.8085	Intermediate Similarity	NPC472930
0.8081	Intermediate Similarity	NPC117185
0.8081	Intermediate Similarity	NPC55872
0.8081	Intermediate Similarity	NPC471005
0.8081	Intermediate Similarity	NPC251017
0.8068	Intermediate Similarity	NPC6707
0.8065	Intermediate Similarity	NPC111585
0.8065	Intermediate Similarity	NPC219495
0.8065	Intermediate Similarity	NPC175628
0.8065	Intermediate Similarity	NPC46758
0.8065	Intermediate Similarity	NPC148414
0.8041	Intermediate Similarity	NPC114274
0.8041	Intermediate Similarity	NPC477854
0.8041	Intermediate Similarity	NPC191565
0.8022	Intermediate Similarity	NPC51014
0.8022	Intermediate Similarity	NPC31564
0.8022	Intermediate Similarity	NPC475022
0.8022	Intermediate Similarity	NPC474778
0.8022	Intermediate Similarity	NPC94462
0.8022	Intermediate Similarity	NPC222613
0.8022	Intermediate Similarity	NPC145879
0.8022	Intermediate Similarity	NPC474732
0.8022	Intermediate Similarity	NPC474733
0.8022	Intermediate Similarity	NPC118648
0.8021	Intermediate Similarity	NPC91439
0.8021	Intermediate Similarity	NPC117133
0.8021	Intermediate Similarity	NPC471463
0.8021	Intermediate Similarity	NPC477853
0.802	Intermediate Similarity	NPC473037
0.8	Intermediate Similarity	NPC240617
0.8	Intermediate Similarity	NPC8993
0.8	Intermediate Similarity	NPC85774
0.8	Intermediate Similarity	NPC184870
0.8	Intermediate Similarity	NPC82902

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 NPC136801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2036
0.2-0.3	4114
0.3-0.4	1963
0.4-0.5	442
0.5-0.6	154
0.6-0.7	180
0.7-0.8	97
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD5328	Approved
0.8202	Intermediate Similarity	NPD4786	Approved
0.8172	Intermediate Similarity	NPD6079	Approved
0.8022	Intermediate Similarity	NPD3618	Phase 1
0.7978	Intermediate Similarity	NPD3667	Approved
0.7938	Intermediate Similarity	NPD4755	Approved
0.7895	Intermediate Similarity	NPD4202	Approved
0.7835	Intermediate Similarity	NPD5222	Approved
0.7835	Intermediate Similarity	NPD4697	Phase 3
0.7835	Intermediate Similarity	NPD5221	Approved
0.7835	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4634	Approved
0.7778	Intermediate Similarity	NPD5285	Approved
0.7778	Intermediate Similarity	NPD5286	Approved
0.7778	Intermediate Similarity	NPD4700	Approved
0.7778	Intermediate Similarity	NPD4696	Approved
0.7755	Intermediate Similarity	NPD5173	Approved
0.77	Intermediate Similarity	NPD5223	Approved
0.7667	Intermediate Similarity	NPD4692	Approved
0.7667	Intermediate Similarity	NPD4139	Approved
0.7634	Intermediate Similarity	NPD5279	Phase 3
0.7624	Intermediate Similarity	NPD5224	Approved
0.7624	Intermediate Similarity	NPD5226	Approved
0.7624	Intermediate Similarity	NPD5225	Approved
0.7624	Intermediate Similarity	NPD5211	Phase 2
0.7624	Intermediate Similarity	NPD4633	Approved
0.7609	Intermediate Similarity	NPD3666	Approved
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3133	Approved
0.7586	Intermediate Similarity	NPD3703	Phase 2
0.7579	Intermediate Similarity	NPD4753	Phase 2
0.7573	Intermediate Similarity	NPD7128	Approved
0.7573	Intermediate Similarity	NPD5739	Approved
0.7573	Intermediate Similarity	NPD6675	Approved
0.7573	Intermediate Similarity	NPD6402	Approved
0.757	Intermediate Similarity	NPD4632	Approved
0.7556	Intermediate Similarity	NPD7525	Registered
0.7549	Intermediate Similarity	NPD4754	Approved
0.7549	Intermediate Similarity	NPD5174	Approved
0.7549	Intermediate Similarity	NPD5175	Approved
0.7528	Intermediate Similarity	NPD6118	Approved
0.7528	Intermediate Similarity	NPD6697	Approved
0.7528	Intermediate Similarity	NPD6115	Approved
0.7528	Intermediate Similarity	NPD6114	Approved
0.7527	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.7476	Intermediate Similarity	NPD5141	Approved
0.7447	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6899	Approved
0.7429	Intermediate Similarity	NPD7320	Approved
0.7429	Intermediate Similarity	NPD6881	Approved
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.7419	Intermediate Similarity	NPD3668	Phase 3
0.7404	Intermediate Similarity	NPD4767	Approved
0.7404	Intermediate Similarity	NPD4768	Approved
0.7391	Intermediate Similarity	NPD4221	Approved
0.7391	Intermediate Similarity	NPD4223	Phase 3
0.7363	Intermediate Similarity	NPD4748	Discontinued
0.7358	Intermediate Similarity	NPD6373	Approved
0.7358	Intermediate Similarity	NPD6372	Approved
0.7358	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5329	Approved
0.7333	Intermediate Similarity	NPD3617	Approved
0.7333	Intermediate Similarity	NPD5701	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7315	Intermediate Similarity	NPD8297	Approved
0.7312	Intermediate Similarity	NPD4788	Approved
0.7303	Intermediate Similarity	NPD6117	Approved
0.729	Intermediate Similarity	NPD7102	Approved
0.729	Intermediate Similarity	NPD7290	Approved
0.729	Intermediate Similarity	NPD6883	Approved
0.7264	Intermediate Similarity	NPD6011	Approved
0.7264	Intermediate Similarity	NPD4729	Approved
0.7264	Intermediate Similarity	NPD5128	Approved
0.7264	Intermediate Similarity	NPD4730	Approved
0.7263	Intermediate Similarity	NPD5690	Phase 2
0.7263	Intermediate Similarity	NPD5280	Approved
0.7263	Intermediate Similarity	NPD4694	Approved
0.7234	Intermediate Similarity	NPD4197	Approved
0.7228	Intermediate Similarity	NPD6083	Phase 2
0.7228	Intermediate Similarity	NPD6084	Phase 2
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7222	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6869	Approved
0.7222	Intermediate Similarity	NPD8130	Phase 1
0.7222	Intermediate Similarity	NPD6847	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6617	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7209	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6009	Approved
0.72	Intermediate Similarity	NPD4629	Approved
0.72	Intermediate Similarity	NPD5695	Phase 3
0.72	Intermediate Similarity	NPD5210	Approved
0.7196	Intermediate Similarity	NPD6014	Approved
0.7196	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6013	Approved
0.7191	Intermediate Similarity	NPD6942	Approved
0.7191	Intermediate Similarity	NPD7339	Approved
0.717	Intermediate Similarity	NPD6412	Phase 2
0.7168	Intermediate Similarity	NPD6054	Approved
0.7168	Intermediate Similarity	NPD6059	Approved
0.7168	Intermediate Similarity	NPD6319	Approved
0.7157	Intermediate Similarity	NPD7638	Approved
0.7156	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.7103	Intermediate Similarity	NPD5168	Approved
0.71	Intermediate Similarity	NPD7748	Approved
0.7093	Intermediate Similarity	NPD5360	Phase 3
0.7093	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD4693	Phase 3
0.7083	Intermediate Similarity	NPD4689	Approved
0.7083	Intermediate Similarity	NPD4688	Approved
0.7083	Intermediate Similarity	NPD4138	Approved
0.7083	Intermediate Similarity	NPD5205	Approved
0.7083	Intermediate Similarity	NPD4690	Approved
0.7079	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6008	Approved
0.7071	Intermediate Similarity	NPD8035	Phase 2
0.7071	Intermediate Similarity	NPD8034	Phase 2
0.7071	Intermediate Similarity	NPD5281	Approved
0.7071	Intermediate Similarity	NPD5284	Approved
0.7064	Intermediate Similarity	NPD5127	Approved
0.7064	Intermediate Similarity	NPD5215	Approved
0.7064	Intermediate Similarity	NPD5216	Approved
0.7064	Intermediate Similarity	NPD5217	Approved
0.7054	Intermediate Similarity	NPD7115	Discovery
0.7043	Intermediate Similarity	NPD6370	Approved
0.7011	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7604	Phase 2
0.6957	Remote Similarity	NPD5983	Phase 2
0.6957	Remote Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD6015	Approved
0.6952	Remote Similarity	NPD7632	Discontinued
0.6941	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6672	Approved
0.6939	Remote Similarity	NPD5737	Approved
0.6932	Remote Similarity	NPD4789	Approved
0.6932	Remote Similarity	NPD4244	Approved
0.6932	Remote Similarity	NPD4245	Approved
0.6923	Remote Similarity	NPD6933	Approved
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7492	Approved
0.6907	Remote Similarity	NPD6684	Approved
0.6907	Remote Similarity	NPD7146	Approved
0.6907	Remote Similarity	NPD7334	Approved
0.6907	Remote Similarity	NPD6409	Approved
0.6907	Remote Similarity	NPD7521	Approved
0.6907	Remote Similarity	NPD5330	Approved
0.6897	Remote Similarity	NPD5988	Approved
0.6893	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD5167	Approved
0.6864	Remote Similarity	NPD6336	Discontinued
0.6864	Remote Similarity	NPD6616	Approved
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6335	Approved
0.6837	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7524	Approved
0.6832	Remote Similarity	NPD5133	Approved
0.6827	Remote Similarity	NPD5696	Approved
0.6818	Remote Similarity	NPD3698	Phase 2
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6868	Approved
0.6814	Remote Similarity	NPD6274	Approved
0.6807	Remote Similarity	NPD8293	Discontinued
0.6807	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD4096	Approved
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7100	Approved
0.6783	Remote Similarity	NPD7101	Approved
0.6768	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD6033	Approved
0.675	Remote Similarity	NPD7736	Approved
0.6735	Remote Similarity	NPD6098	Approved
0.6733	Remote Similarity	NPD6050	Approved
0.6733	Remote Similarity	NPD6411	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6703	Remote Similarity	NPD6926	Approved
0.6703	Remote Similarity	NPD6924	Approved
0.6703	Remote Similarity	NPD5733	Approved
0.6702	Remote Similarity	NPD7645	Phase 2
0.6702	Remote Similarity	NPD4195	Approved
0.67	Remote Similarity	NPD6080	Approved
0.67	Remote Similarity	NPD6673	Approved
0.67	Remote Similarity	NPD6904	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