NPASS Compound

Structure

NPC138756 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 1.6984 -3.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 -4.4677 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 -0.5909 -2.0032 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 -0.9000 -2.9543 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 -1.2601 -1.2601 0.0000 C 0 0 2 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 -0.2308 -3.6974 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 0.7473 -3.4895 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 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -4.6485 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 1.0563 -2.5385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 29 1 0 0 0 0 15 20 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 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 31 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 32 1 6 0 0 0 24 30 1 0 0 0 0 24 33 2 0 0 0 0 25 26 1 0 0 0 0 25 34 1 1 0 0 0 27 35 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.3
Volume:	530.133
LogP:	4.664
LogD:	4.392
LogS:	-4.238
# Rotatable Bonds:	9
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	6.4
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.668
MDCK Permeability:	1.846268969529774e-05
Pgp-inhibitor:	0.427
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	96.01363372802734%
Volume Distribution (VD):	1.122
Pgp-substrate:	2.078763484954834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.412
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	7.424
Half-life (T1/2):	0.597

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.762
Carcinogencity:	0.093
Eye Corrosion:	0.088
Eye Irritation:	0.051
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: NPC138756

Natural Product ID:	NPC138756
*Common Name:**	Fasciculol H
IUPAC Name:	(2R,3R,5R,10S,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,3-dihydroxy-4,4,10,13,14-pentamethyl-1,2,3,5,6,7,11,15,16,17-decahydrocyclopenta[a]phenanthren-12-one
Synonyms:
Standard InCHIKey:	DHYNMMKCYKLJKR-LDKSJVRISA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-17(9-12-23(32)27(4,5)35)18-13-14-29(7)19-10-11-22-26(2,3)25(34)21(31)16-28(22,6)20(19)15-24(33)30(18,29)8/h17-18,21-23,25,31-32,34-35H,9-16H2,1-8H3/t17-,18-,21-,22+,23-,25+,28-,29+,30+/m1/s1
SMILES:	C[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:	CHEMBL2375642
PubChem CID:	72714436
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[556018]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[556018]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[556018]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	9860.0	nM	PMID[556018]

☑ 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 NPC138756 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	178
0.1-0.2	1435
0.2-0.3	5681
0.3-0.4	15715
0.4-0.5	7083
0.5-0.6	6281
0.6-0.7	4868
0.7-0.8	1262
0.8-0.85	147
0.85-0.9	40
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC136801
0.9205	High Similarity	NPC200702
0.907	High Similarity	NPC32830
0.9059	High Similarity	NPC99909
0.8953	High Similarity	NPC44181
0.8941	High Similarity	NPC72133
0.8941	High Similarity	NPC89077
0.8902	High Similarity	NPC22403
0.8864	High Similarity	NPC189520
0.8851	High Similarity	NPC77263
0.8851	High Similarity	NPC250592
0.8837	High Similarity	NPC469314
0.8837	High Similarity	NPC241875
0.8837	High Similarity	NPC469317
0.8837	High Similarity	NPC90652
0.8804	High Similarity	NPC316964
0.875	High Similarity	NPC289213
0.875	High Similarity	NPC469400
0.8736	High Similarity	NPC143767
0.8736	High Similarity	NPC471722
0.8736	High Similarity	NPC131470
0.8736	High Similarity	NPC242864
0.8736	High Similarity	NPC471724
0.8736	High Similarity	NPC470417
0.8721	High Similarity	NPC28252
0.8721	High Similarity	NPC94755
0.8721	High Similarity	NPC55309
0.869	High Similarity	NPC7988
0.8652	High Similarity	NPC155304
0.8636	High Similarity	NPC86319
0.8636	High Similarity	NPC474245
0.8636	High Similarity	NPC275740
0.8621	High Similarity	NPC187376
0.8621	High Similarity	NPC159046
0.8621	High Similarity	NPC233836
0.8605	High Similarity	NPC197823
0.8588	High Similarity	NPC86370
0.8539	High Similarity	NPC191684
0.8539	High Similarity	NPC183283
0.8523	High Similarity	NPC193360
0.8506	High Similarity	NPC472491
0.8506	High Similarity	NPC473168
0.8506	High Similarity	NPC472494
0.8488	Intermediate Similarity	NPC473246
0.8488	Intermediate Similarity	NPC59453
0.8488	Intermediate Similarity	NPC221758
0.8478	Intermediate Similarity	NPC249954
0.8462	Intermediate Similarity	NPC318332
0.8462	Intermediate Similarity	NPC166906
0.8444	Intermediate Similarity	NPC233116
0.8444	Intermediate Similarity	NPC297265
0.8444	Intermediate Similarity	NPC23434
0.8444	Intermediate Similarity	NPC473166
0.8444	Intermediate Similarity	NPC63748
0.8427	Intermediate Similarity	NPC229871
0.8427	Intermediate Similarity	NPC469319
0.8427	Intermediate Similarity	NPC1015
0.8427	Intermediate Similarity	NPC31985
0.8427	Intermediate Similarity	NPC474889
0.8427	Intermediate Similarity	NPC102414
0.8427	Intermediate Similarity	NPC475921
0.8427	Intermediate Similarity	NPC77168
0.8427	Intermediate Similarity	NPC84271
0.8427	Intermediate Similarity	NPC474704
0.8421	Intermediate Similarity	NPC477915
0.8421	Intermediate Similarity	NPC473424
0.8409	Intermediate Similarity	NPC475740
0.8409	Intermediate Similarity	NPC474684
0.8409	Intermediate Similarity	NPC142361
0.8404	Intermediate Similarity	NPC110149
0.8391	Intermediate Similarity	NPC474083
0.8391	Intermediate Similarity	NPC470574
0.8391	Intermediate Similarity	NPC478127
0.837	Intermediate Similarity	NPC473170
0.837	Intermediate Similarity	NPC297199
0.837	Intermediate Similarity	NPC259286
0.837	Intermediate Similarity	NPC317586
0.837	Intermediate Similarity	NPC255809
0.837	Intermediate Similarity	NPC470016
0.8353	Intermediate Similarity	NPC6707
0.8352	Intermediate Similarity	NPC274046
0.8352	Intermediate Similarity	NPC69454
0.8352	Intermediate Similarity	NPC198074
0.8352	Intermediate Similarity	NPC475255
0.8351	Intermediate Similarity	NPC323834
0.8333	Intermediate Similarity	NPC175628
0.8333	Intermediate Similarity	NPC191892
0.8333	Intermediate Similarity	NPC111585
0.8333	Intermediate Similarity	NPC20388
0.8333	Intermediate Similarity	NPC148414
0.8315	Intermediate Similarity	NPC53911
0.8315	Intermediate Similarity	NPC328539
0.8295	Intermediate Similarity	NPC31564
0.8295	Intermediate Similarity	NPC475022
0.8295	Intermediate Similarity	NPC145879
0.8295	Intermediate Similarity	NPC51014
0.8295	Intermediate Similarity	NPC222613
0.8295	Intermediate Similarity	NPC474778
0.8295	Intermediate Similarity	NPC118648
0.8295	Intermediate Similarity	NPC474732
0.8295	Intermediate Similarity	NPC474733
0.828	Intermediate Similarity	NPC305483
0.828	Intermediate Similarity	NPC117133
0.828	Intermediate Similarity	NPC95565
0.828	Intermediate Similarity	NPC7124
0.828	Intermediate Similarity	NPC328162
0.828	Intermediate Similarity	NPC96859
0.8276	Intermediate Similarity	NPC214043
0.8276	Intermediate Similarity	NPC82902
0.8276	Intermediate Similarity	NPC85774
0.8272	Intermediate Similarity	NPC201373
0.8261	Intermediate Similarity	NPC469406
0.8261	Intermediate Similarity	NPC8993
0.8261	Intermediate Similarity	NPC245972
0.8261	Intermediate Similarity	NPC174051
0.8261	Intermediate Similarity	NPC67831
0.8261	Intermediate Similarity	NPC196485
0.8261	Intermediate Similarity	NPC111015
0.8256	Intermediate Similarity	NPC151519
0.8256	Intermediate Similarity	NPC30166
0.8247	Intermediate Similarity	NPC209502
0.8247	Intermediate Similarity	NPC204833
0.8242	Intermediate Similarity	NPC86266
0.8242	Intermediate Similarity	NPC272746
0.8242	Intermediate Similarity	NPC168027
0.8242	Intermediate Similarity	NPC110657
0.8242	Intermediate Similarity	NPC19114
0.8242	Intermediate Similarity	NPC473167
0.8242	Intermediate Similarity	NPC475806
0.8242	Intermediate Similarity	NPC473998
0.8242	Intermediate Similarity	NPC26888
0.8242	Intermediate Similarity	NPC107690
0.8242	Intermediate Similarity	NPC185936
0.8242	Intermediate Similarity	NPC212301
0.8242	Intermediate Similarity	NPC262870
0.8235	Intermediate Similarity	NPC236112
0.8222	Intermediate Similarity	NPC309603
0.8222	Intermediate Similarity	NPC473999
0.8222	Intermediate Similarity	NPC122116
0.8222	Intermediate Similarity	NPC215029
0.8222	Intermediate Similarity	NPC54689
0.8222	Intermediate Similarity	NPC220498
0.8222	Intermediate Similarity	NPC76879
0.8222	Intermediate Similarity	NPC476733
0.8202	Intermediate Similarity	NPC58063
0.8202	Intermediate Similarity	NPC317590
0.8202	Intermediate Similarity	NPC472493
0.8193	Intermediate Similarity	NPC73875
0.8191	Intermediate Similarity	NPC122294
0.8191	Intermediate Similarity	NPC320306
0.8182	Intermediate Similarity	NPC471224
0.8182	Intermediate Similarity	NPC474218
0.8172	Intermediate Similarity	NPC45324
0.8172	Intermediate Similarity	NPC162001
0.8172	Intermediate Similarity	NPC184848
0.8172	Intermediate Similarity	NPC472485
0.8172	Intermediate Similarity	NPC37787
0.8172	Intermediate Similarity	NPC180557
0.8172	Intermediate Similarity	NPC271195
0.8172	Intermediate Similarity	NPC473415
0.8172	Intermediate Similarity	NPC48330
0.8172	Intermediate Similarity	NPC473648
0.8172	Intermediate Similarity	NPC30677
0.8172	Intermediate Similarity	NPC469329
0.8172	Intermediate Similarity	NPC127063
0.8172	Intermediate Similarity	NPC222845
0.8172	Intermediate Similarity	NPC69548
0.8163	Intermediate Similarity	NPC149047
0.8163	Intermediate Similarity	NPC171137
0.8163	Intermediate Similarity	NPC152695
0.8163	Intermediate Similarity	NPC97202
0.8163	Intermediate Similarity	NPC202167
0.8163	Intermediate Similarity	NPC85829
0.8163	Intermediate Similarity	NPC302607
0.8163	Intermediate Similarity	NPC319077
0.8163	Intermediate Similarity	NPC49958
0.8163	Intermediate Similarity	NPC260268
0.8163	Intermediate Similarity	NPC50692
0.8163	Intermediate Similarity	NPC214264
0.8163	Intermediate Similarity	NPC150531
0.8163	Intermediate Similarity	NPC296945
0.8163	Intermediate Similarity	NPC476027
0.8163	Intermediate Similarity	NPC48733
0.8163	Intermediate Similarity	NPC166607
0.8161	Intermediate Similarity	NPC472743
0.8161	Intermediate Similarity	NPC278648
0.8161	Intermediate Similarity	NPC132635
0.8161	Intermediate Similarity	NPC475726
0.8161	Intermediate Similarity	NPC472492
0.8161	Intermediate Similarity	NPC476082
0.8161	Intermediate Similarity	NPC207013
0.8152	Intermediate Similarity	NPC474806
0.8152	Intermediate Similarity	NPC470376
0.8152	Intermediate Similarity	NPC275809
0.8152	Intermediate Similarity	NPC170220
0.8152	Intermediate Similarity	NPC243866
0.8152	Intermediate Similarity	NPC472930
0.8152	Intermediate Similarity	NPC109305
0.8152	Intermediate Similarity	NPC107674
0.8152	Intermediate Similarity	NPC141497

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 NPC138756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1954
0.2-0.3	4128
0.3-0.4	2031
0.4-0.5	441
0.5-0.6	160
0.6-0.7	169
0.7-0.8	107
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8488	Intermediate Similarity	NPD4786	Approved
0.8427	Intermediate Similarity	NPD5328	Approved
0.8295	Intermediate Similarity	NPD3618	Phase 1
0.8256	Intermediate Similarity	NPD3667	Approved
0.8242	Intermediate Similarity	NPD6079	Approved
0.8152	Intermediate Similarity	NPD4202	Approved
0.8	Intermediate Similarity	NPD4755	Approved
0.7931	Intermediate Similarity	NPD4692	Approved
0.7931	Intermediate Similarity	NPD4139	Approved
0.7895	Intermediate Similarity	NPD5222	Approved
0.7895	Intermediate Similarity	NPD4697	Phase 3
0.7895	Intermediate Similarity	NPD5221	Approved
0.7895	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD5279	Phase 3
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7835	Intermediate Similarity	NPD4700	Approved
0.7835	Intermediate Similarity	NPD5286	Approved
0.7835	Intermediate Similarity	NPD4696	Approved
0.7835	Intermediate Similarity	NPD5285	Approved
0.7826	Intermediate Similarity	NPD4753	Phase 2
0.7816	Intermediate Similarity	NPD7525	Registered
0.7812	Intermediate Similarity	NPD5173	Approved
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6399	Phase 3
0.7755	Intermediate Similarity	NPD5223	Approved
0.7711	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5211	Phase 2
0.7677	Intermediate Similarity	NPD5225	Approved
0.7677	Intermediate Similarity	NPD5226	Approved
0.7677	Intermediate Similarity	NPD4633	Approved
0.7677	Intermediate Similarity	NPD5224	Approved
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.766	Intermediate Similarity	NPD7515	Phase 2
0.764	Intermediate Similarity	NPD4223	Phase 3
0.764	Intermediate Similarity	NPD4221	Approved
0.7624	Intermediate Similarity	NPD5739	Approved
0.7624	Intermediate Similarity	NPD7128	Approved
0.7624	Intermediate Similarity	NPD6675	Approved
0.7624	Intermediate Similarity	NPD6402	Approved
0.7614	Intermediate Similarity	NPD4748	Discontinued
0.76	Intermediate Similarity	NPD5175	Approved
0.76	Intermediate Similarity	NPD5174	Approved
0.76	Intermediate Similarity	NPD4754	Approved
0.7586	Intermediate Similarity	NPD3617	Approved
0.7582	Intermediate Similarity	NPD5329	Approved
0.7558	Intermediate Similarity	NPD6117	Approved
0.7556	Intermediate Similarity	NPD4788	Approved
0.7525	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.7476	Intermediate Similarity	NPD6881	Approved
0.7476	Intermediate Similarity	NPD6899	Approved
0.7476	Intermediate Similarity	NPD7320	Approved
0.7473	Intermediate Similarity	NPD4197	Approved
0.7471	Intermediate Similarity	NPD6116	Phase 1
0.747	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4767	Approved
0.7451	Intermediate Similarity	NPD4768	Approved
0.7449	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD6083	Phase 2
0.7442	Intermediate Similarity	NPD7339	Approved
0.7442	Intermediate Similarity	NPD6942	Approved
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7423	Intermediate Similarity	NPD5695	Phase 3
0.7404	Intermediate Similarity	NPD6372	Approved
0.7404	Intermediate Similarity	NPD6373	Approved
0.7386	Intermediate Similarity	NPD6115	Approved
0.7386	Intermediate Similarity	NPD6114	Approved
0.7386	Intermediate Similarity	NPD6118	Approved
0.7386	Intermediate Similarity	NPD6697	Approved
0.7379	Intermediate Similarity	NPD5697	Approved
0.7379	Intermediate Similarity	NPD5701	Approved
0.7358	Intermediate Similarity	NPD8297	Approved
0.7349	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5360	Phase 3
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7326	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7748	Approved
0.7312	Intermediate Similarity	NPD4688	Approved
0.7312	Intermediate Similarity	NPD4689	Approved
0.7312	Intermediate Similarity	NPD4138	Approved
0.7312	Intermediate Similarity	NPD5205	Approved
0.7312	Intermediate Similarity	NPD4690	Approved
0.7312	Intermediate Similarity	NPD4693	Phase 3
0.7308	Intermediate Similarity	NPD4729	Approved
0.7308	Intermediate Similarity	NPD5128	Approved
0.7308	Intermediate Similarity	NPD6011	Approved
0.7308	Intermediate Similarity	NPD4730	Approved
0.7292	Intermediate Similarity	NPD8034	Phase 2
0.7292	Intermediate Similarity	NPD5284	Approved
0.7292	Intermediate Similarity	NPD5281	Approved
0.7292	Intermediate Similarity	NPD8035	Phase 2
0.729	Intermediate Similarity	NPD4632	Approved
0.7264	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6650	Approved
0.7264	Intermediate Similarity	NPD6869	Approved
0.7264	Intermediate Similarity	NPD6649	Approved
0.7264	Intermediate Similarity	NPD6847	Approved
0.7264	Intermediate Similarity	NPD8130	Phase 1
0.7264	Intermediate Similarity	NPD6617	Approved
0.7262	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7241	Intermediate Similarity	NPD3703	Phase 2
0.7238	Intermediate Similarity	NPD6013	Approved
0.7238	Intermediate Similarity	NPD6014	Approved
0.7238	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD6882	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4245	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.7176	Intermediate Similarity	NPD4244	Approved
0.717	Intermediate Similarity	NPD5251	Approved
0.717	Intermediate Similarity	NPD5250	Approved
0.717	Intermediate Similarity	NPD5169	Approved
0.717	Intermediate Similarity	NPD5249	Phase 3
0.717	Intermediate Similarity	NPD5247	Approved
0.717	Intermediate Similarity	NPD5248	Approved
0.717	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5135	Approved
0.7159	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6933	Approved
0.7158	Intermediate Similarity	NPD5737	Approved
0.7158	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5168	Approved
0.7128	Intermediate Similarity	NPD7521	Approved
0.7128	Intermediate Similarity	NPD7334	Approved
0.7128	Intermediate Similarity	NPD6684	Approved
0.7128	Intermediate Similarity	NPD7146	Approved
0.7128	Intermediate Similarity	NPD6409	Approved
0.7128	Intermediate Similarity	NPD5330	Approved
0.7103	Intermediate Similarity	NPD5215	Approved
0.7103	Intermediate Similarity	NPD5127	Approved
0.7103	Intermediate Similarity	NPD5216	Approved
0.7103	Intermediate Similarity	NPD5217	Approved
0.71	Intermediate Similarity	NPD7902	Approved
0.7075	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3698	Phase 2
0.7048	Intermediate Similarity	NPD6412	Phase 2
0.7041	Intermediate Similarity	NPD5133	Approved
0.703	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD5696	Approved
0.701	Intermediate Similarity	NPD4096	Approved
0.6979	Remote Similarity	NPD6903	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD6098	Approved
0.6939	Remote Similarity	NPD6050	Approved
0.6937	Remote Similarity	NPD6009	Approved
0.6932	Remote Similarity	NPD5733	Approved
0.6932	Remote Similarity	NPD6924	Approved
0.6932	Remote Similarity	NPD6926	Approved
0.6923	Remote Similarity	NPD7645	Phase 2
0.6923	Remote Similarity	NPD4195	Approved
0.6909	Remote Similarity	NPD5167	Approved
0.6907	Remote Similarity	NPD6673	Approved
0.6907	Remote Similarity	NPD6080	Approved
0.6907	Remote Similarity	NPD6904	Approved
0.6903	Remote Similarity	NPD6319	Approved
0.6903	Remote Similarity	NPD6054	Approved
0.6903	Remote Similarity	NPD6059	Approved
0.6897	Remote Similarity	NPD4243	Approved
0.6897	Remote Similarity	NPD4758	Discontinued
0.6875	Remote Similarity	NPD6335	Approved
0.6848	Remote Similarity	NPD4695	Discontinued
0.6847	Remote Similarity	NPD6868	Approved
0.6847	Remote Similarity	NPD6274	Approved
0.6837	Remote Similarity	NPD5692	Phase 3
0.6827	Remote Similarity	NPD7632	Discontinued
0.6814	Remote Similarity	NPD7101	Approved
0.6814	Remote Similarity	NPD7100	Approved
0.6813	Remote Similarity	NPD3671	Phase 1
0.6813	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5364	Discontinued
0.6804	Remote Similarity	NPD4518	Approved
0.68	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD6008	Approved
0.6786	Remote Similarity	NPD6317	Approved
0.6783	Remote Similarity	NPD6370	Approved
0.6782	Remote Similarity	NPD4747	Approved
0.6771	Remote Similarity	NPD4623	Approved
0.6771	Remote Similarity	NPD4519	Discontinued
0.6768	Remote Similarity	NPD6411	Approved
0.6768	Remote Similarity	NPD5694	Approved
0.6742	Remote Similarity	NPD4784	Approved
0.6742	Remote Similarity	NPD4785	Approved
0.6742	Remote Similarity	NPD4687	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