NPASS Compound

Natural Product: NPC195224

Natural Product ID	NPC195224
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SLJNSLIEGINNEE-UWUOQQJISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL308259
PubChem CID	10055179
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 92 95 0 0 0 0 0 0 0 0999 V2000 -3.6938 0.3904 2.4541 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1580 1.3641 1.4953 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9572 1.0860 0.1954 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9708 -0.3587 0.1069 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1576 -0.7288 -1.1353 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7305 -0.4599 -1.1449 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3215 -0.3188 -2.6407 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0347 -1.8091 -0.8195 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4456 -1.5974 -0.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0901 -0.4940 -1.2787 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2730 0.7514 -1.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7101 1.9040 -1.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0619 0.5465 -0.3665 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4765 1.7416 0.3273 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4236 2.7826 -0.0761 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7502 3.5503 1.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7764 2.7491 1.9051 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3826 3.2159 2.9042 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7827 2.3549 -0.5735 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 2.3055 -2.0482 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9398 3.2493 -0.2249 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5180 1.4888 1.7445 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4304 1.8190 2.6608 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4694 2.4075 2.2345 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2794 1.5111 4.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3562 -0.2544 -0.6304 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5435 -0.3250 -1.3023 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5561 -0.6062 -2.5242 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8427 -0.0774 -0.6295 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8173 0.2174 0.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0129 0.4800 1.4238 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2585 0.4369 0.8573 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3934 0.6945 1.6233 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2385 0.9903 2.9483 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9908 1.0333 3.5152 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8634 0.7834 2.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1443 -2.6956 -1.8833 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5821 -4.0090 -1.8145 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9134 -4.4778 -0.7191 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6449 -4.8306 -3.0588 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5645 -2.0424 -1.4706 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3986 -2.3522 -2.5428 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -1.3856 -3.2420 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8337 -3.7009 -2.9070 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2691 -0.9188 -0.1574 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6801 -2.0673 0.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9280 -2.6404 1.3194 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0060 -2.6960 0.2683 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7772 0.9590 3.4397 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7834 0.1554 2.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0770 -0.4565 2.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5096 -0.9579 0.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6530 -0.1161 -1.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2811 -0.1392 -3.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 -1.2156 -3.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2717 0.5636 -2.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4379 -2.2685 0.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9516 -2.5520 -0.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6566 -1.5884 0.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2803 -0.7213 -2.3261 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6916 1.9376 -1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2214 2.8583 -1.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3792 -0.0710 0.5251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4968 2.3614 0.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0542 3.5355 -0.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8950 3.6403 1.8978 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0100 4.6021 1.0063 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7451 1.8862 -2.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8853 2.0536 -2.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9242 3.4074 -2.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7038 2.7164 0.4269 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6154 3.4837 -1.1145 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7336 4.2211 0.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6417 0.4907 4.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8087 1.5230 4.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7371 2.2782 4.7587 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7621 -0.1337 -1.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8548 0.2690 1.1739 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4236 0.2059 -0.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3638 0.6564 1.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1317 1.1936 3.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8714 1.2675 4.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8971 0.8240 3.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4493 -5.5754 -2.9579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3593 -5.3302 -3.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -4.2300 -3.9575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5945 -4.3856 -2.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9416 -3.6669 -3.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3076 -3.9884 -3.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5676 -2.6070 1.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8097 -3.7934 0.1379 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5406 -2.3004 -0.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 15 19 1 0 19 20 1 0 19 21 1 0 14 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 10 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 8 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 5 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 4 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 17 2 1 0 36 31 1 0 19 3 1 0 13 6 1 0 1 49 1 0 1 50 1 0 1 51 1 0 4 52 1 1 5 53 1 6 7 54 1 0 7 55 1 0 7 56 1 0 8 57 1 1 9 58 1 0 9 59 1 0 10 60 1 6 12 61 1 0 12 62 1 0 13 63 1 1 14 64 1 1 15 65 1 6 16 66 1 0 16 67 1 0 20 68 1 0 20 69 1 0 20 70 1 0 21 71 1 0 21 72 1 0 21 73 1 0 25 74 1 0 25 75 1 0 25 76 1 0 29 77 1 0 30 78 1 0 32 79 1 0 33 80 1 0 34 81 1 0 35 82 1 0 36 83 1 0 40 84 1 0 40 85 1 0 40 86 1 0 44 87 1 0 44 88 1 0 44 89 1 0 48 90 1 0 48 91 1 0 48 92 1 0 M END

Standard InCHIKey	SLJNSLIEGINNEE-UWUOQQJISA-N
Standard InCHI	InChI=1S/C37H44O11/c1-19-27(42)17-26-33(45-22(4)39)32-20(2)28(48-30(43)16-15-25-13-11-10-12-14-25)18-29(44-21(3)38)37(32,9)35(47-24(6)41)34(46-23(5)40)31(19)36(26,7)8/h10-16,26,28-29,32-35H,2,17-18H2,1,3-9H3/b16-15+/t26-,28-,29-,32-,33+,34+,35-,37+/m0/s1
SMILES	CC1=C2[C@H]([C@@H]([C@]3(C)[C@H](C[C@@H](C(=C)[C@H]3[C@@H]([C@H](CC1=O)C2(C)C)OC(=O)C)OC(=O)/C=C/c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.29	Volume:	679.337 ? Van der Waals volume.
Dense:	0.978	LogP:	3.407 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.195 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.125 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	31.0
TPSA:	148.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.17	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.671	Fsp³:	0.514
MCE-18:	118.75 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.918	Fluc inhibitor:	0.425 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.131 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.089 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.304	Promiscuous compounds:	0.104

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.077	MDCK Permeability:	-4.734
Pgp-inhibitor:	1.0	Pgp-substrate:	0.06
PAMPA:	0.211 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.874
Plasma Protein Binding (PPB):	90.509%	Volume Distribution (VD):	-0.303
Fu:	8.977% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.006
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.262
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.082
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.253 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.021

Half-life (T1/2):

0.561

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.745	Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.624	Skin Sensitization:	0.998
Carcinogencity:	0.531	Eye Corrosion:	0.002
Eye Irritation:	0.133	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.284	Ototoxicity:	0.523
Hematotoxicity:	0.621	Drug-induced Nephrotoxicity:	0.973
Genotoxicity:	0.948	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.183	Hek293 Cytotoxicity:	0.1
BCF:	0.589 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.686 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.715 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.177 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plantsci.2006.08.002]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(01)00432-0]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	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	Organism Name	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
IC50	2

Activity Type	# Activity
Cell line	4

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell line	KB 3-1	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[12217376]
NPT1178	Cell line	KB 3-1	Homo sapiens	ED50	=	4.1	ug ml-1	PMID[12217376]
NPT137	Cell line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	DOI[10.1016/S0960-894X(97)00029-2]
NPT168	Cell line	P388	Mus musculus	IC50	=	10000000.0	nM	DOI[10.1016/S0960-894X(97)00439-3]

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC195224 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	13764
0.1-0.2	33209
0.2-0.3	2644
0.3-0.4	183
0.4-0.5	26
0.5-0.6	19
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8028	Intermediate Similarity	NPC473439
0.7917	Intermediate Similarity	NPC607515
0.7432	Intermediate Similarity	NPC472361
0.7067	Intermediate Similarity	NPC472437
0.6667	Remote Similarity	NPC475493
0.6585	Remote Similarity	NPC472371
0.65	Remote Similarity	NPC472388
0.6375	Remote Similarity	NPC473443
0.6375	Remote Similarity	NPC472418
0.6282	Remote Similarity	NPC473749
0.6203	Remote Similarity	NPC300827
0.6049	Remote Similarity	NPC471758
0.593	Remote Similarity	NPC475400
0.5926	Remote Similarity	NPC45821
0.5875	Remote Similarity	NPC472394
0.5862	Remote Similarity	NPC80895
0.5854	Remote Similarity	NPC284022
0.5854	Remote Similarity	NPC225103
0.5802	Remote Similarity	NPC469742
0.5765	Remote Similarity	NPC93632
0.5595	Remote Similarity	NPC209851
0.5529	Remote Similarity	NPC471880
0.5529	Remote Similarity	NPC472373
0.5529	Remote Similarity	NPC473541
0.5479	Remote Similarity	NPC608702
0.5325	Remote Similarity	NPC472389
0.5301	Remote Similarity	NPC472395
0.52	Remote Similarity	NPC143609
0.5176	Remote Similarity	NPC473423
0.5161	Remote Similarity	NPC301946
0.5055	Remote Similarity	NPC266374

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC195224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3875
0.1-0.2	5160
0.2-0.3	115
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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