NPASS Compound

Structure

NPC77296 OpenBabel06302215272D 61 69 0 0 1 0 0 0 0 0999 V2000 -6.1592 0.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1811 0.7269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8720 -0.2241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8939 -0.4321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2248 0.3111 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8180 -0.6025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3180 -1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8235 -0.4979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6156 0.4802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6211 0.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2143 -0.3288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7367 -0.6378 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4799 0.0313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4309 -0.2777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6388 -1.2559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5899 -1.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7978 -2.5430 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0547 -3.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1036 -2.9031 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8957 -1.9250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1525 -2.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9446 -1.6160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2015 -2.2851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7496 -1.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9575 -0.9979 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3642 -1.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 -3.5723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4094 -3.2632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2015 -2.2851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7496 -1.9761 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4927 -2.6452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2848 -3.6234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3338 -3.9324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4438 -2.3362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9575 -0.9979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9446 -1.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7367 -0.6378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4799 0.0313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2719 1.0095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3209 1.3185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4223 0.6493 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3733 0.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2143 -0.3288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1130 2.2966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0151 1.6786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8072 2.6567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5503 3.3259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3424 4.3040 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3914 4.6130 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6482 3.9439 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3028 4.2529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5108 5.2311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8561 2.9658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1834 5.5912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0856 4.9731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5014 3.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4309 -0.2777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7489 -2.8520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4816 0.9802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5338 1.2621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5119 1.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 61 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 5 4 1 1 0 0 0 5 59 1 0 0 0 0 5 6 1 0 0 0 0 5 60 1 0 0 0 0 6 7 1 6 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 1 0 0 0 9 59 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 20 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 58 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 28 33 1 0 0 0 0 29 30 1 0 0 0 0 29 36 1 0 0 0 0 30 31 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 0 0 0 0 31 34 1 0 0 0 0 32 33 1 0 0 0 0 37 36 1 6 0 0 0 37 38 1 0 0 0 0 37 43 1 0 0 0 0 38 39 1 0 0 0 0 38 57 1 1 0 0 0 39 40 1 0 0 0 0 39 45 1 1 0 0 0 40 41 1 0 0 0 0 40 44 1 6 0 0 0 41 42 1 1 0 0 0 41 43 1 0 0 0 0 46 45 1 6 0 0 0 46 47 1 0 0 0 0 46 53 1 0 0 0 0 47 48 1 0 0 0 0 47 56 1 1 0 0 0 48 49 1 0 0 0 0 48 55 1 6 0 0 0 49 50 1 0 0 0 0 49 54 1 1 0 0 0 50 51 1 6 0 0 0 50 53 1 0 0 0 0 51 52 1 0 0 0 0 60 61 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	868.45
Volume:	836.733
LogP:	1.568
LogD:	1.914
LogS:	-3.983
# Rotatable Bonds:	7
TPSA:	255.91
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	6.855
Fsp3:	0.909
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.222
MDCK Permeability:	6.983264756854624e-05
Pgp-inhibitor:	0.406
Pgp-substrate:	0.303
Human Intestinal Absorption (HIA):	0.958
20% Bioavailability (F20%):	0.181
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	44.28028106689453%
Volume Distribution (VD):	0.306
Pgp-substrate:	32.16534423828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.528
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	0.483
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.635
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.779
Skin Sensitization:	0.795
Carcinogencity:	0.651
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC77296

Natural Product ID:	NPC77296
*Common Name:**	KEBKEYDWZYNHHS-KNQIUGTDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KEBKEYDWZYNHHS-KNQIUGTDSA-N
Standard InCHI:	InChI=1S/C44H68O17/c1-18-8-11-44(55-16-18)19(2)30-27(61-44)14-25-23-7-6-21-12-22(46)13-29(43(21,5)24(23)9-10-42(25,30)4)58-41-38(32(49)26(47)17-54-41)60-40-36(53)37(31(48)20(3)56-40)59-39-35(52)34(51)33(50)28(15-45)57-39/h6,19-20,22-41,45-53H,1,7-17H2,2-5H3/t19-,20-,22+,23+,24-,25-,26-,27-,28+,29+,30-,31-,32-,33+,34-,35+,36+,37+,38+,39-,40-,41-,42-,43-,44+/m0/s1
SMILES:	C=C1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](C[C@H]([C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)O2)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	13935613
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO25265	Sophora secundiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)78784-3]
NPO26956	Crambe crambe	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00019a049]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11325235]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[14575439]
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	Stems	n.a.	n.a.	PMID[14695805]
NPO26683	Dichomitus squalens	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620268]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18442289]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547115]
NPO24883	Angiopteris caudatiformis	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19371069]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20581114]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25515814]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	Underground parts	n.a.	n.a.	PMID[9784168]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26915	Erinus alpinus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2096	Stenostomum acutatum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26862	Pentaceraster alveolatus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25729	Centaurea aemulans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26693	Daphne papyracea	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23570	Hypolaena fastigiata	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26427	Heterocapsa triquetra	Species	Heterocapsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25210	Fulmarus glacialis	Species	Procellariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26489	Arthrobacter viscosus	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26683	Dichomitus squalens	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18404	Clarkia unguiculata	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24883	Angiopteris caudatiformis	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29139	Agave huachucensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24509	Randia longispina	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26300	Penianthus zenkeri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26467	Nipaecoccus aurilanatus	Species	Pseudococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12552	Aloe indica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26444	Mimosa invisa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26793	Trichia carnea	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25265	Sophora secundiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24150	Baptisia lecontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26915	Erinus alpinus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26222	Gonepteryx rhamni	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23463	Basanacantha spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26956	Crambe crambe	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27038	Senecio macrophyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23068	Guettarda eximia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27000	Geranium macrorrhizum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27053	Maclura aurantiaca	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25843	Solanum chacoense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25025	Gypothamnium pinifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24594	Polypodium hastatum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26843	Heliconius cydno	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25783	Tulipa silvestris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26577	Clinostemon mahuba	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24375	Micrococcus luteus	Species	Micrococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25438	Xiphophora gladiata	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20000	Adina rubescens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27027	Renilla muelleri	Species	Renillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26020	Dahlstedtia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25592	Pedicularis densispica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26106	Lactarius pubescens	Species	Russulaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC77296 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	317
0.1-0.2	2111
0.2-0.3	6317
0.3-0.4	13504
0.4-0.5	9312
0.5-0.6	5909
0.6-0.7	2993
0.7-0.8	1450
0.8-0.85	434
0.85-0.9	212
0.9-0.95	79
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID

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 NPC77296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2238
0.2-0.3	4235
0.3-0.4	1630
0.4-0.5	434
0.5-0.6	271
0.6-0.7	56
0.7-0.8	12
0.8-0.85	7
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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